Weirdly enough, there always seemed to be more upskirt opportunities in the days before smartphones. Probably because women were less on guard, and the internet wasn't around to tell them all the things guys are up to.
Still, so many of my best memories are from that time. One of my first jobs was working in a grocery store, stocking the shelves and moving random boxes wherever the manager wanted them. She was a tall woman, with brown hair and a curvy, but fit, body. She almost always wore professional flowing skirts that came down to her knee.
Well, one day, being the young guy I was, I noticed how focused she was as the annual corporate inspection was approaching. She had me running around doing whatever she needed. When I came back to tell her I'd finished, I noticed she was on a ladder dusting the top of the employee lockers. Her back was to me, and she had no idea I was there.
So, I crouched down and had a look up her skirt.
She was wearing a blue bikini panties that were giving her a slight wedgie from her walking around all day. The cotton fabric was tight around her pussy, because I could just make out the outline of her lips. I honestly couldn't tell you how long I stayed down there. It could've been ten seconds, could've been a whole five minutes. She just didn't notice.
Eventually, not wanting to get caught, I stood back up and pretended to walk in for the first time. She was surprised and thanked me for my work.
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