[Dookieman]

College years-->Ashley (curvy, lighter-skin tone black girl) from the band - freshman year, I spotted Ash on her way back to the dorm; I was on that way out as well, so we made small-talk while walking together. This one was another surprise in terms of the outfit---Ash was a shy/quiet "nice girl" type...like you wouldn't expect her to wear extremely revealing or wild clothing...but that day she had on an extremely short, flimsy skirt. I knew the chances of seeing something NICE were about to get good as we headed outside...

..and yep, I already knew it was going to be windy that day (haha I was/am such an upskirt freak that yes, I even paid attention to the weather conditions just to be aware of possible "windy upskirt" potential on any given day.) Anyway, her little skirt was flared and flimsy, and only came to an inch or 2 above her mid-thigh point! Sure enough, as we were outside, the wind kept playing with her skirt. Naturally, I made sure to be slightly behind her (this was a bit natural since I made sure to be the "gentleman" and open the door to let her go first...HAHA) I kept getting flashes of her great little ass-cheeks and panties... they were pink; not quite a thong but not bloomers either...I guess kinda medium coverage but still "cheeky" like a pink bikini. She kept having to reach back and put the skirt down. I never thought I would see that much of her but damn that was a nice view. There was a segment of stairs outside as well, which made the view even better from the back. There were moments of some nervous laughter as she was probably embarrassed, likely thinking "well, I'm never wearing this stupid skirt again!"....and she had no idea how hard this was making me at the time while trying to carry on the conversation with her. It never got up above her waist but the flashes were at times putting about half her ass/panties on display. Shortly after we got up the stairs and closer to the dorm, I had exploded after seeing all those flashes and her reactions to them.

Neighbor-- Anne Hathaway clone?! Upskirt---
At an old apartment... there was one incredible hot one that lived upstairs... I never knew her personally or even her name but she looked kinda like that actress Anne Hathaway, but with a better, slightly curvier body. She had a short flared black skirt (the "skater skirt" that was quite popular at that time of the earlier 2000s)... I couldn't resist... I made sure to just happen to be headed downstairs at the same time she was coming up. She was on the phone at the time so that helped the situation of her most likely not noticing me that much. As she headed up 1 flight of stairs I went down and looked up and there it was... saw right up the back of that little skater-skirt.... wonderful view of the entire backside of her legs, right up the thighs to the ass. Her panties were very skimpy; looked like a white thong, with the cheeks slightly jiggling with each step. It didn't take long at all for this one; in seconds I had busted a huge load to that visual. Unfortunately I never saw her again though.