Twenty years ago I had a friend who lived two doors away. I was 13 and a virgin. His mother was a slender, quite pretty, women who was always friendly and had a sexy smile. In the eighties, BMX was the biggest craze of the day and me and my friend would always go out playing on our bikes. One day I got a puncture and took the bike to my friend’s house to fix it.
I had to go in the kitchen to use one of his mum’s bowls to put the inner-tube in water to see where the puncture was. My friend was outside and I was in the kitchen with my hands in the bowl. His mother came in and asked me if I wanted some help fixing the puncture. She was wearing a pink towelling dressing gown and slippers. Initially, she bent down to help me but then after a few seconds she squatted down and started looking for the puncture. Her legs were spread wide apart and her bum was nearly touching the kitchen as she squatted. I looked between her legs and saw her gorgeous, soft, pink pussy as clear as day. Her lips were slightly parted and gently framed by her dark brown pubic hair. She was so engrossed in finding the puncture and fixing it, I just stared at this amazing upskirt sight without a break for about 5 minutes. I saw every single millimetre of her pussy and pussy-lips as she moved hers legs slightly to keep herself on balance. My cock was rock-solid in my trousers and ready to spunk. I was almost in a state of shock and completely speechless as I’d never seen a woman’s pussy that close in my life. I’ve never been so turned-on and so nervous. When we’d finished, She went back to putting the family laundry back in the washing basket and I put the tyre back on my bike. I then went into their toilet to have a wank and came in about 3 seconds (give or take a second). My friend and I went out to play for the rest of the day and I never ever mentioned it to him. Me and my family moved about 3 years later and I’ve only ever seen her once since. She was walking across the road with her husband while I drove by in my car. Only about 10 years later did I ever think that she might of done it on purpose and that she got a kick out of it. She must of known that 20 years later I would still wank-myself-off thinking about her spread legs and her beautiful pussy.

December 30th, 2007
Categories: Upskirt Stories . Author: deve8 . Comments: No Comments

I am fortunate to live in an almost perfect venue for upskirts. The island of Kauai is tropical and the temperature rests at a mean of about 80 Fahrenheit all year around. Because of this, women wear short skirts twelve months out of the year. The island style favors dresses that are flimsy and gauzy as well as extremely short, tourists from colder climates who are unaccustomed to wearing such garments tend to make quite a few mistakes when they’ve got a few mai tais under their belts.
To add to the delight, many (perhaps most) buildings in the tourist town of Hanalei are raised several feet off the ground due to excessive flooding during the rainy season. As I walk along the street, I am at eye level with the legs of any woman sitting on the verandah of a restaurant, bar or shop. You can imagine the results. Last summer, for example, I caught sight of a woman sitting at the local burger stand. She was in her early or middle thirties, with bright red hair and an attractive face characterized by thick, pouty lips. She was more than a bit plump, though not precisely fat, and dressed in one of those flimsy little tropical dresses I have already mentioned. When I first spotted her, she was seated next to her husband or boyfriend, munching a burger. Her legs were wide open and I was treated to a luscious view of panties even brighter red than her hair.
I lingered in front of the burger stand, pretending to study the sky, the pedestrian traffic, even the cars rolling down the road. I feasted on a view of panties until I felt that I was beginning to look a bit conspicuous just standing there. I circled round the line of shops, returned for another look, but discovered that she was gone. I went on about my business, running some mundane errands. In so doing, I happened to walk by another popular restaurant with a verandah, and there was Big Red again! The burger stand didn’t serve alcohol, and hubby or boyfriend apparently wanted a beer, so there they were, and once again those bright red panties flashed in front of my eyes. I watched her raise a glass of brew, her face flushed, big lips parted in a smile. She shook her red hair. This gal just couldn’t seem to keep her legs closed. I circled the restaurant a couple of times without feeling especially conspicuous. After all, Hanalei is full of locals who simply loiter around town all day long. But soon she was gone.
Well, it had been a good day. Two sightings within an hour. Time to move on, though. But then I thought to pay a visit to my housekeeper who worked part time at an art gallery. As I approached the gallery, lo and behold! The red-haired flasher was sitting in a rattan chair in front of the gallery while her male companion looked at paintings. She was fanning herself in the hot sun. Once again, her legs were open to reveal a magnificent red triangle in full glory. Shortly after, the man emerged and off they went. I didn’t see them again. But I couldn’t help wondering about it all.
A woman can easily flash through carelessness once in a day. If she’s on vacation and feeling loose, maybe twice. But three times within an hour? And splendid views in every case? I can’t help thinking she was doing it on purpose.

October 15th, 2007
Categories: Upskirt Stories . Author: berukckp . Comments: No Comments

School was very fruitful in my early years and one teacher, a Miss Watt, was a great favourite. I reckon she must have been around 30 years old, slim with brown hair and glasses. She wasn’t particularly nice looking but I didn’t care! My desk was right in front of her table at the front of the class and I spent a lot of time dropping my pencil and rubber on the floor so that I could get under her desk and look up her grey pleated skirt. She must have known what I was up to but never gave and signs of it. She normally sat with her legs crossed, but her nylon underskirt was always hanging down which was enough to get me going. It was always light blue, so either she had more than one or did infrequent washing! On most occasions I also got a glimpse of her stocking tops with occasionally a little bit of bare thigh above. On one, unfortunately only one, momentous occasion she uncrossed and re-crossed her legs the other way just as I was under the desk. I like to think that she did it intentionally as she did it quite slowly and deliberately and I got a wonderful flash of her knickers, which were light blue nylon. That was almost 40 years ago and I still think of if sometimes when I’m having a wank.

October 8th, 2007
Categories: Upskirt Stories . Author: Nicky . Comments: No Comments

A little story that always does it for me when I think of it.

About 18 months ago we were at a birthday party for one of my friends. The night was going well and the group of 7 of us were sitting around a table getting quite merry. My lady Sue had been away from the table, she returned and my friend grabbed her arm and pulled her onto his knee. I didn’t mind at first but then he put his hand on her leg. I felt quite annoyed and so reached out for his girl and pulled her onto my knee. I put my hand on her leg and said to him that feels better. He started to run his hand higher up her leg and I followed suit saying that we had discovered a new game called Mirror Images.

I was going to do everything he was.

In front of the others there our hands started to run over the women’s legs, sides, backs. Nothing too obvious but just running our fingers along the line of the bras and counting blouse buttons by touching them. Our friends at the table were sitting watching and almost speechless. Then I started to slowly ease his woman’s skirt up her legs and he followed suit by slowly opening the split in the overlapping skirt of my woman. More and more leg was exposed until at the same time both pairs of knickers came into view. You could see the Red lace of my girlfriends thong and the white panties his girlfriend was wearing.

The atmosphere was crackling with tension and at that point the person who’s birthday it was came over and broke the moment. Everyone separated and we guys around the table crossed our legs and even the girls were squirming a bit on their seats. In my mind it’s just as sexy to be fully dressed as it is to be naked if you do it right.

You should try playing Mirror Images sometime. It’s great fun!

October 1st, 2007
Categories: Upskirt Stories . Author: bohus sykora . Comments: No Comments

It was a Friday night a week before Christmas and with strong breezes predicted and lots of scantily ladies bound to be out, I hit the town. I’d watched a couple of girls struggling with floaty skirts but most had successfully clung on. A snowstorm was clearly brewing up, the cool air became very still and a few flakes of snow started to fall. Gradually, the flakes got bigger and the breeze strengthened again. I noticed the girl stood in a doorway of a nightclub chatting to a friend. She had a black strappy top on and a plaid denim miniskirt. The design of it meant that whilst it COULD flare out, it would need a subway grate or leaf blower shoved up her arse to move it.

One of the biggest turn-ons in this situation is sheer unexpectedness of being upskirted. You can tell the ones who realise their mistake early on and spend the rest of the day/night holding on to, smoothing down or resting their handbag against their skirt. She didn’t seem to be doing any of this, she just stood in the doorway with the strong breeze having little affect on the skirt. It was barely an inch below her arse. I’m not sure why, but the two girls walked away from the club entrance together, possibly to another bar. What happened next I hear you ask?

The girls walked up towards a T-junction in the road. The snow wasn’t actually falling, it was just swirling around. It actually seemed as if an updraft was blowing flakes back up into the sky – I’m sure its an image we’ve all seen – anyway, seeing her walk towards this updraft made me wonder just what would happen to that skirt!

The wind suddenly strengthened as she stepped into its path. Im sure the snow blowing around her face didn’t help her either. With no warning, the whole of her skirt was simply catapulted up to her chest! It was almost like a funhouse airgrate, if she’d been wearing a knee-length skirt, it would have ended up round her ears, so strong was the gust.

Not only was the back up, showing everyone her thonged arse, but it was up at the front and sides as well – basically a 360 degree view for everyone. If fact, such was the height her skirt had blown, a centimetre or so of flesh could be seen ABOVE the thong. One problem these days is that a small flash of bare butt cheeks doesn’t always confirm the colour (or existence) of a thong – there was no doubt here!

After a split-second of sheer disbelief, she squealed and grabbed the front of her skirt, the problem being that the wind had now pinned the back of it to her, keeping her arse on display for a good 5 seconds. Realised there was no other way out, she slumped to the ground by a wall, still being buffeted by the wind but with her friend helping her hold the skirt in place. The two of them giggled and screamed there on the ground for about a minute or so, before she got to her feet and walked on with both hands virtually pinning the skirt down just in case…..

I rate this as my favourite upskirt of all time, not least because of the sheer embarrassment of it all. Reaction is all important to me – Having a skirt blow up in the wind is a bit like a practical joke to me – the best people are shocked at first, very red faced, but have the ability to laugh it off.

September 25th, 2007
Categories: Upskirt Stories . Author: merx . Comments: No Comments