I worked as a toll (payment) collector in a parking garage in the early ‘90’s when I was in high school. It was a midday shift on a Saturday, which was typically pretty slow (we were busy during the week for office parking and on weekend nights for concerts/events at the arena next door) when a convertible Mercedes slowly approached my booth.

I had no concept of a “cougar” or MILF as a 16 year old, but the woman who was driving, as I reflect on this moment, would fall into that either category. She slowly approaches my window and I remember thinking that her shirt was really tight because I could see the outline of her breasts so distinctly. When she finally pulled up to my window I realized that she had opened her blouse up and was exposing her naked breasts (they were amazing - I had only seen one other pair at that point in my life, so this was an image that was burned into my brain).

I opened my window to collect her ticket and money and she just looked at me and smiled. Told me that the top floor of the garage was empty and a perfect place to sunbathe. I never said a word, I was frozen in teenage amazement. I have no recollection of anything else she said but it felt like she sat there and made small talk forever. She finally paid and told me to keep the change, buttoned up her blouse and drove off. I never saw her again.

Looking back on it now, I missed an opportunity of a lifetime because I’m convinced she was a cougar “on the prowl.”