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Wearing skirts and flashing your panties

Middle School

Posted by adamkessler2 on 2016-08-08 18:37:52

When I was in middle school, there was a very pretty girl I had a huge crush on. One day, towards the end of the semester, she wore a mid-thigh level skirt of loose, flowing fabric. It was really memorable because she never worse skirts or dresses.

As a teenage boy at the time, I'm sure it surprises no one that I spent every chance I had that day taking a look at her beautiful legs. It's not that she was a prude or dressed overly conservative; she did wear shorts and tight jeans all the time. It's just that a skirt was so noteworthy because I had always noticed she never wore one, yet always wished she would.

At recess that day, she decided to play four square -- which she also never did. She wasn't a tom-boy at all, and we rarely had girls play. Now for people not familiar with four square, the object is to keep getting people in the square ahead out until you reach the serving square. As she was a pretty girl amongst a bunch of boys, no one played hard against her and she made it to the server.

I was in the #2 square at the time. On one serve, the motion of her arm flipped up the front of her skirt. I'll never, ever forget the pink panties she was wearing. But it didn't flip just momentarily. It got caught in the breeze and the whole skirt, front and back was blown up for several seconds. She was flailing her arms around trying to get it under control. It looked like when someone gets an umbrella blown inside-out and struggles to invert it. I got a nice lengthy look and was beyond overjoyed -- taking in her lovely thighs, the shape of her hips, and of course her pretty pink panties. And I never stopped being obsessed with getting to look up girls' skirts ever since.

I have no idea what got into her that day to both wear a skirt she never wore before, and play a playground game she never played before either. I thank my lucky stars she did though, and that I was there to see it.