It was the early '90s, and I was committed to making my way in the business world before addressing my lack of a social life. While I spent the majority of my off hours horny, most of my energy was saved for the job and learning the trade. One encounter during that period stands out among all the rest, but it had absolutely nothing to do with the work.
Being athletic myself, I was friends with almost everyone at the firm with any type of athletic ability, and I casually became acquainted on the softball field with a secretary named Laura who worked in another department of the firm. Laura was a cute strawberry blonde a couple of years my senior, and I was in complete lust for her. Unfortunately, I knew nothing could or would ever happen because she was way out of my league. Here I was, mid-20s, fresh out of business school, 5'8" tall and sporting the beginnings of a beer belly. My hair was already thinning, and it was clear that I would be bald in less that 5 years. She, on the other hand, was mid-30s, stood 5'5" and, I am guessing weighed 110 lbs soaking wet. She wasn't overly busty, and I would guess she was about 34B-24-34. Her blonde curls always seemed to end up sexily falling down over her eyes so she often looked at you through her locks.
Everything about her screamed sex, and she flirted like a pro. On more than one occasion, I had to take matters into my own hands once I got home after a softball game. I remember one game in particular when she came over to me in the dugout, stepped between my legs and sat down on my knee, put her arms around my neck and whispered in my ear. You cannot imagine how difficult it is to wear a cup with a hard on.
The sad part about the end of the softball season was that I would not get to see Laura or get to playfully flirt with her. One day, though, I ran into Laura in the hallway on my side of the building. She explained that she was delivering something for her boss and seemed really down. On an impulse, I invited her to lunch, and she readily accepted.
So, there we were about an hour later driving to lunch at an upscale restaurant about a mile from the firm. On the ride over, we chatted and the flirting picked up right where it had left off on the softball field. She told me about her ex-husband (I didn't even know she had been married), and she went on in great detail about what a fantastic lover he was. Funny, I don't remember asking, but I was happy to have her bring up sex. She also felt compelled to tell me about another secretary she worked with who was a virgin, or as she put it, had never had a man "cross her threshold."
We got seated at the restaurant, and the sexual innuendos and conversation continued. She told me she was good friends with Mary, another quite attractive woman on the team. Laura swore me to secrecy and then proceeded to tell me what an exhibitionist Mary was.
One time, she told me, the two of them were in a bar and made the acquaintance of some guy next to them. After several margaritas, Mary blurted out that she had just bought a new bra and panty set and asked if the guy would like to see them. Apparently being no fool, he said sure, so she proceeded to lift her sweater and show him, and anyone else in the bar who might be interested, the lacy black Victoria's Secret demi bra (whatever that is) that she was wearing. She then turned and lifted her skirt to provide him a glimpse of her shapely behind in the matching panties. I could only imagine how hot she looked and the reaction of all of the male patrons in the bar.
Laura told me that Mary then had looked over at her and told her to show him her bra, too. Laura begged off, saying that she couldn't because, and I quote, "I don't wear underwear." I just about swallowed my tongue. Here was this gorgeous creature of a women confessing to me that, very likely, as we sat there at the table in the restaurant, me in my business suit and her in a frilly short dress, she was braless and pantyless.
Now, being pretty inept and inexperienced with anything relating to women, I could only hope that she was trying to not so gently nudge me into making a move. I didn't, however, want to make any assumptions or take any steps that could get me fired or accused of sexual harassment. But I was harder than I had ever been and would not be able to walk out of the restaurant without putting on quite a show. I decided not to risk it, and we finished our meal. Luckily the swelling subsided, albeit slowly because she was a very touchy person, variously touching my arm, my leg, my shoulder.
The check came, I paid it, and we headed for the car. On the way, we passed a fire hydrant. Not unusual, of course, but Laura did something that completely took me by surprise. As we came abreast of the hydrant, she lifted her dress and then her leg like a dog relieving himself and giggled. I got the quickest of glimpses of the inside of her well turned thigh, unfortunately not enough to see for myself whether she was in fact wearing panties.
We got in the car, though, and I couldn't think of anything but the possibility that her bare pussy was a mere few inches away, resting comfortably on the leather passenger seat of my car. Finally, I couldn't stand it any more and I looked over at her.
"Do you really not wear underwear?" I asked
"Don't you believe me?" she replied without missing a beat, a devilish grin on her face.
She had me now, although it had taken me some time to get there. I had to see where this might take me, the job be damned.
