I miss my upskirt era. My time at Catholic high school definitely gave me a fetish that's going to last forever. I was an awkward nerd who wasn't gonna be getting laid, so I got my kicks from looking up the uniform skirts, mostly on the stairs. Suddenly I found all these girls hot and they were all wearing this article of clothing I never really noticed before, and it presented the possibility of a certain interesting type of exposure. The skirts were pleated and many girls wore them quite short, so they had a lot of play and movement that allowed for plenty of glimpses.

Eventually I made a list of girls at school and all the panties I'd seen each of them wearing. (I wish I still had that, but I must've deleted it when I thought this was all cringe. Now I don't care anymore lol.) I got too brazen and even developed a reputation as a perv among some of the girls who realized what I was doing. I remember entering the building one day and this hot girl was headed up the stairs, and I immediately planned to head down the stairs to look up her skirt, but first she saw me, kind of made a face, and held her skirt against her butt as she went upstairs. Oh well, I remember seeing her dark green panties once.

One of the cheerleaders wore her skirt super short, and I have so many good memories. One time she was standing on her tiptoes to brush the snow off her car with her her blue-green panties peeking out from under her skirt. Another time we put our desks in a circle for a class and she sat across from me and gave me an incredible spread-leg view of her light purple panties for minutes on end. I'm pretty sure she didn't intend to give me a treat and was just careless.

There was also my biggest crush. I looked up her skirt all the damn time, and she definitely knew about my habit, because one time she covered her butt when I was behind her, but then she seemed to stop caring and let me have my fun. My favorite panties of hers were grey with red trim. She was always sweet to me and gives me hugs when we see each other, though she's married now. Sometimes I wonder about the conversation that we'll never have about my perving on her in high school. Ah well.

At a restaurant over the weekend, noticed two middle-aged women having their meal, one wearing a very short dark blue sporty skirt, so I assumed it had built-in shorts under it.

Nope, as they were leaving, she made eye contact with me, spread her legs all the way open to get out of the booth, I looked down, saw her light blue panties and max-pad wings over the sides with her messy bush trying to escape. I closed my eyes thinking, "I know she caught me, but I did NOT need to see that, so I hope she didn't think I was a perv who enjoyed the view because she would be completely wrong."

But it was forgotten soon after when we were leaving and a 40-something woman in the waiting area had a tank top on with mile-long nipples poking out. That was much more pleasant.

That is how you get punished for peeping 😆😅🤣😂

The funny part is that I didn't want to look and didn't have any intention of looking, but it was the whole looking at a train wreck thing. lol

Well I guess that often happens when guys flash. A guy flashes his dick to a lady who stares with big wide open eyes. The guy thinks the lady is overwhelmed seeing his big beautiful fat juicy dick. The lady sees the bloody train wreck 😆

Holding the new baby
 

My girlfriend and I have just had a baby. While it has filled me with boundless joy, it has also severely limited my voyeuristic opportunities. But, it has made up for that by finally giving me a good look up a woman's skirt that I have been trying to catch for years.

I've talked about her before here: https://forum.oneclickchicks.com/sho...49#post3300549

So she came over to see the new baby, and she had on a long flower dress that went down to her ankles. My girlfriend was in our bedroom, sitting on the bed breast feeding it. I led her into the room, and "Anita" kneeled on the corner of the bed watching. Sensing an opportunity, I went around and climbed on the corner of the bed between the two of them and motioned for the baby to burp because they were finished feeding. After burping for a few seconds, Anita put one knee on the bed and another foot on the ground to get closer to see the baby. Because her dress was so long, she had to hike it up to get in this pose, and that's when I sensed that it could actually happen. At that moment, my gf looked at me and said "should we go into the living room". I knew that this would ruin my chance, so I just stalled and pretended to listen to Anita saying whatever she was saying.

Then, I asked Anita "Do you want to hold the baby?" She was nervous because she's never held a baby that young before, so she climbed onto the bed and that's when it started. she swung her thighs open wide and i saw right up to her crotch about 2 feet away. She had on dark green bikini cut panties, and they were so hot. She then proceeded to shuffle a little closer, causing her skirt to ride up even more, and she sat cross-legged right in front of me and reached for the baby from my hands. She then sat there, just like that, for about 5 minutes.

At one point, she announced "Hey I'm spreading my legs wide, so Sky44444, don't look!" I just smiled and played dumb, and my girlfriend just said "It's fine", and the show continued.

I've been trying to see up this woman's skirt for maybe 4 years since I met her. I'm so glad it finally happened!

The VERY first time I saw up my wife's sister's skirt was when we had a brand new baby. She had never held a baby before, so she slid to the front of the couch, opening her legs wide to steady herself, showing off her light blue panties under her dark blue jean skirt. She realized what she did and tried to close her legs, but she was unsteady, so she opened them again. Later that day, my wife said, "I can't believe I saw up my own sister's skirt!" Funny thing is that I have seen up her skirt over 100 times since then.

I saw up my MIL's dress last night. I had to pick the cat up off the floor, and the cat tried to run left, so I was on my knees and bent forward even more, lost my balance, happened to glance towards my MIL, and her legs were spread wide, showing me her very shiny, white, very loose panties. She noticed that I was looking, so she closed her legs quickly, but then opened them again for some reason. I didn't necessarily enjoy it (I have seen her totally naked before, though...long story).

Man oh man I hope this happens to me! I'm praying that because she's already "broken the seal" that she'll be way more nonchalant from now on. I think the fact that she called out that her legs were wide open in front of me and said "don't look" in a joking way and continued to show the goods for a while afterwards with no awkwardness at all is very promising. Even more so that all this happened in front of my girlfriend and she had a "who cares" attitude.

All of my fingers and toes are crossed that this event opens the flood gates.

Ya, you never know. If either of them are anything like my wife and her sister, prepare to be forever confused. My wife will often have a "who cares?" attitude, just to actually care a lot more the next time. And my wife's sister even commented out loud "I don't care!" when I was caught looking into her gaping bra once, only for her to care much more ever since, but then simultaneously gives up trying to hide it other times.

But I wish good luck to you!

Baby and pets are the most treasurable moments to see up girls skirts.
I can't even remember how many times I've been look up my female friends skirts with the chances like it. Gotta grab it tight when the chances come.