This is an upskirt I saw when I was a grad student at college.
This girl (about 25/26 at the time) was in a nearby office to me, and I used to sit with her and other friends in the tea-room. She was slightly geeky and shy; her face was not the most attractive around, but she had a lovely body- nice perky breasts, and very nice long legs.
I knew she had nice legs because in the summer, she often wore short denim skirts with no tights. The rest of her dress was pretty conservative, apart from these short skirts. Even so, she was pretty careful, and knew how to sit in a short skirt without showing her knickers.
But one day, I happened to be sitting in the perfect position- opposite her, and quite close. The angle was just right- as she I sat there, I had a slight view between her legs... and what I saw there surprised me. Her knickers were white cotton, but I could see a little picture of a teddy bear on them- a very cutesy sort of picture that you wouldn't expect a women of 25 to want on her knickers! Somehow it seemed appropriate for this girl who wore short skirts but seemed very shy underneath.
Sadly I never saw up her skirt properly again, so I didn't find out if she often wore these very girly knickers. But I still have the thought of that teddy bear stretched tight over her pussy.
------------------------
P.S. This reminds me of a similar story, though it isn't an upskirt. I knew a girl in the last year of school (we were 18), let's call her Anna. She was a 'good girl' who was quite flirty at the same time.
Basically, Anna got accidentally X-rayed in a photograph. Someone had taken a drunken photo at a party, showing Anna facing away from the camera. She had been wearing tight, light-coloured trousers, and somehow the flash had gone through the material, and clearly showed the colourful pattern of shooting stars on Anna's panties... the sort of little-girly knickers that many of the girls in the Sixth-form wouldn't be seen dead wearing.
Anna didn't seem too bothered about the photo- actually, I had once heard her comment before on the fact she wore girly knickers. A guy had cheekily asked one of the girls what colour knickers she was wearing, and Anna said "I think I've got... fairies on mine."
It was nice to learn from the X-ray photo that this was probably true; she really did have knickers with some cutesy pattern on, and not only that- she was telling the boys about it in a vaguely flirty way.
