[Voyeur] Upskirt stories

[rudolfm]

I would rather assume she wanted to try showing a bit. You being the little brother she was probably sure you wouldn't grab her so she felt safe.

[Bigfatdude]

Yeah quite possibly- it’s hard to imagine she was so naive that she didn’t consider that I would be able to see everything up her skirt- either way it’s pretty hot! Either she flashed her ass and thong to me and still has no idea or did it on purpose knowing I would see her delicious ass in a pink thong!

[island]

Originally Posted by Bigfatdude

This upskirt happened 20 years ago but is still something I think about when wanking.

So I was 18 and my sister in law would have been 28. We are in the UK and she was classic private school girl, from the south, very well spoken etc. she had been going out with my bro a few years and always worn very demure clothing- very rarely wore skirts or tops that would show cleavage etc. you could tell she had an amazing body though and very pretty face. About 5 foot 8 with long legs and porcelain skin.

I was back that summer from university and ended up staying with them for a bit. As the weather got warmer she did start to wear some skirts that showed a bit of leg. Nothing too short but short enough for me to catch a glimpse of thing when she sat down and crossed legs etc. Nothing close to an upskirt though.

However that all changed a little later that summer. She was putting stuff up in the loft and asked me to help. She had a loose fitting skirt that went a little above the knee. She also had a white top on that wasn’t quite long enough to cover the back and as we were getting boxes sorted etc I could see a pink thong at the back of her skirt peeking up. That alone would have been enough for me to wank over as the thought of her wearing thongs was exciting enough.

However as we started putting things up in the attic I realised what was going to happen. They were the type of metal stairs you have to pull down to access the attic and she said she would stand on the stairs and put things up as I passed them. As she climbed higher up the stairs I could see a full view up her skirt as it fanned out a little. This revealed her small pink thong and a full view of her arse and also a clear view from the front of her crotch area. This was repeated as she went up and down the stairs and I got so hard. Once we finished I went to the bathroom and wanked which took about 30 seconds to cum.

I always wondered a couple of things about this

1) She must have known I would be able to see up her skirt.
2) I was going through some personal stuff at the time and wondered if this was her way of taking pity
3) was it a way to try to seduce me- her and my bro always argued and in some way would ha e been her revenge.


They are still together- I have had the odd upskirt glimpse of her over the years but nothing like that summer and whilst I’ve seen up many skirts since nothing has compared!

Ah this made me remember the time my be loved colleguage fixing a shower room window. She is a bit short and have very beauty butt. With the opened window high above then she had to take a chair to stand up to fix the glass. At that time I passed behind her back but she was too much focus on fixing window. And I had my chance to take some upskirt picture with the girl I adore in short skirt and red panty. This is the first time I knew that her red panty looks like small thong. I still so much adore her till now with some upskirt pictures along the years....

[Gnome72141]

At a restaurant last night, and the table diagonal from me set up a fun view of this woman who was getting up and sitting down often. It was a corner booth, so a lot of movement to let people in and out of the corner.

When she first arrived, she was VERY careful about getting into the booth...she had a black short-ish tight skirt on (she was probably late 40s, fit, well-kept, but looked annoyed at her husbands). I didn't see anything, not that I was trying too hard.

Then she got up to give a hug to someone who arrived later, and she was very careful getting up.

But then she slid back into the booth, and she had her legs spread VERY wide to get around the pole holding up the table, and there were her dark blue full coverage panties. She looked up at me and saw me looking in her direction, closed her legs, and gave me the "I don't really care but I wasn't trying to give you a view" expression on her face.

She got up a few more times during dinner, and half the time she was very careful, and half the time she wasn't.

[Gnome72141]

Just a simple one: My wife's best friend was over the other day wearing a skirt. It was probably the third time seeing her in a skirt in the 10 years that I have known her. The previous two times, she was wearing shorts under her skirt, so I assumed she was this time, too.

I was feeling faint, so I laid down on the floor in front of her. Not to look up her skirt, but because I was really feeling faint.

As I was about to get up, I told myself to guess which color shorts she was wearing this time. I noticed that her legs were spread open, and no shorts, so I looked anyway...she was wearing actual very basic white panties!

She caught me looking, quickly closed her legs, then stood up a moment later, but opening her legs wide to get her balance before standing up.

My wife was glaring at me because I think she thought that I intentionally put myself on the floor to look up her skirt when that wasn't true at all. I really was about to faint, and I just happened to catch her undies on the way up.

It may be another ten years before she wears a skirt again...or she might wear one again the next time I see her. (She used to wear many layers, then one time I made some joke about wearing white t shirts with bright bras underneath, and her friend started doing exactly that...so now 1/2 the time we see her, she is in white tank tops with brightly colored bras underneath!)

[arsicus]

Originally Posted by Gnome72141

Not to look up her skirt, but because I was really feeling faint.

Sure buddy

[Gnome72141]

Originally Posted by arsicus

Sure buddy

Totally serious. I have a heart condition that required surgery, and recovery hasn't been going well, to say the least.

[piecenick]

I used to work with these two ladies doing the timekeeping on a construction site. One was older, not very attractive, one was 21, very smart and country girl pretty. We worked in a trailer that even with AC, was warm in the summer.

Lynn, the young one, wore these light summer, cotton dresses to try to keep comfortable, she always looked cute and sexy. She was a free spirit, more than once I wondered if she was bare under the dress.

One day is was hotter than usual, the AC just couldn’t handle it. The cool air was delivered by vents in the trailer floor. In her light dress Lynn tried to cool off by standing over an air vent, the velocity of the air was more than she expected, it blew her skirt up high enough for me to get a view of her trimmed bush. It took her a second to compose herself, step off the vent and push her dress down. She yelled and blushed, but Marilyn Monroe could not have been sexier.

[rudolfm]

Originally Posted by piecenick

She yelled and blushed, ...

That is what I love about US girls. If they notice they are showing they make lots of noise and all guys look 😆
European girls stay cool and most guys miss the fun.

[Ingloriousb]

So I’ve been friends with this woman (I have put up a couple of posts of her face) a few years now and built up a good amount of trust. We’ve never had sex (unfortunately as she has an amazing body) but we’ve become close and she’s confided a lot in me over the years.

We met in the park a couple of summers ago for a catch up with some other friends- my friend had on a tiny denim skirt showing off her gorgeous legs- milk white, thin and long but not skinny. I positioned myself opposite her to ensure the best view and we all sat on a picnic blanket. She did initially try to hide her modesty and cover up but inevitabley her skirt was so small and tight it revealed lovely patterned knickers- white with small red hearts. She even then drew attention to her legs and talked about how she worked out and wanted to get them tanned etc. I got such an amazing view all afternoon right up her skirt and it was a great day!