Memories
 

Durban-South Africa-Apartheid. Cape Town/Durban many British (Ex-Service) Immigrant Families. Visiting Warship, Decks Ceremonially Lined, met at the very end of the Outer Breakwater by "The Lady in White". Megaphone to hand, she Patriotically Serenades you, strolling alongside before finally standing in her car and accompanying you ALL THE WAY into the Port. Salutes Exchanged, Ensigns Dipped as you Pass. Many cars, mostly open-topped, waiting on the jetty with girls (bikinis/topless) standing on the seats and waving. Hundreds of heavily scented "Up-Homer" Invites arrive onboard. Numerous "Front-Line" Old Comrades want to Pay their Respects. Hence "Ship open to Visitors". Young Ladies wishing to meet "someone like Daddy" form "The Old Country". You're 7000 miles, and many months away from Home. And you are not yet half-way into your South Atlantic Commission ! OK.

I think this story is perfect for this thread.
My wife and I are on vacation with one of my closest friends and his family (wife and teenage son). With this couple we have a family relationship, like brothers and sisters with no sexual aspects, to be honest my friend's wife is not attractive.
One evening after dinner we sit on the floor to talk (yoga position). My wife is wearing the dress in the first photo. My friend is sitting across from my wife and I notice that he keeps looking at her between her legs. But my wife is sitting composed, her dress is not short (but it is transparent in the photo you can almost see the underpants) and you can't see anything. When my wife gets up I see that my friend looks carefully between her legs waiting for an upskirt but it doesn't happen because my wife is careful. For the first time I understand that my friend also has a sexual attraction to my wife.
The next night my wife is wearing the white pants in the second photo. They are completely transparent, in the photo you can also see the red label on the underpants. We take a long walk through the village and the two women often walk in front. My friend enjoys my wife's ass and panties for at least ten minutes. The village has neon lights and the transparency is even more evident. I think he enjoyed the show as he was waiting for the upskirt the night before.
The next night was even better. My wife is wearing the mini dress in the third photo. After dinner I invite everyone to sit at the bar on armchairs and I make sure that my friend and I are facing my wife. My wife sits down, stays for a few seconds as in the third photo clearly showing her panties, it's a perfect upskirt, then she crosses her legs completely showing her panties for a moment and in the end she's left with only her thighs uncovered.
I expect a series of upskirts in the following minutes but this is not the case. My wife receives a phone call, answers, uncrosses her legs, shows her panties again for a few seconds, then she gets up again with one final upskirt and walks away to talk. The phone call lasts a few minutes eventually my friend and wife leave before my wife sits down again. It could have been better but in the end I am satisfied for the few amazing upskirts my friend has seen. I think he liked it too.

Fantastic! What a treasure she must be.

I'd love to read more in more detail, but this already paints a vivid picture ;).

Crab hunting
 

We were on the beach crab hunting one night and I was using my phone as my flashlight with video going in case the wind blew her skirt up. We came across another family and they kind of tagged along for a short while with us. While the other husband and I were on the ground digging for a crab, she came over chasing a crab and bent over right in front of us. So since he had a flashlight where we were digging, I turned my phone up so that it shined up her dress and acted like I didn’t know where it was pointing. He tried to act like he wasn’t looking but I know he got an eyeful of her ass and pussy. She also bent over with a crab in her hand and showed the crab to the group, and you could see right down her dress.

Crab hunting
 

We were on the beach crab hunting one night and I was using my phone as my flashlight with video going in case the wind blew her skirt up. We came across another family and they kind of tagged along for a short while with us. While the other husband and I were on the ground digging for a crab, she came over chasing a crab and bent over right in front of us. So since he had a flashlight where we were digging, I turned my phone up so that it shined up her dress and acted like I didn’t know where it was pointing. He tried to act like he wasn’t looking but I know he got an eyeful of her ass and pussy. She also bent over with a crab in her hand and showed the crab to the group, and you could see right down her dress.

WOW! She has a really nice pussy!

Couples night
 

My wife (Charlotte) and I occasionally meet up with a mate of mine who I've known since school and his wife (Amy), we're all in our late 20's and both couples have been together for a while. I sometimes meet up with just my mate and we inevitably end up talking about our wives after a couple of pints, I've got the impression from these chats that my mate quite fancies my wife, and to be fair, she is stunning! Now for years I've had this thing where I just really want him to see my wife's knickers, I've occasionally been tempted to just show him a picture of my wife in her underwear, however, i don't want things to get awkward so I've always thought that an "accidental" flash would be much better. Unfortunately, there's just never been the opportunity...until a few weeks ago.

We met up with them in a bar in town which was fairly new and none of us had been to before, Amy was wearing a short black dress and Charlotte looked incredible in a short, red bodycon dress. We all arrived around the same time and were taking in out surroundings when we all noticed the staircase which went over several tables (including ours) and up to a mezzanine level where there was another bar. As we looked over to the staircase a girl was walking up in a skirt, now the design of this staircase was essentially like a row of shelves with gaps between each step, presumably to keep it from blocking all the light. This however meant that any time a woman in a skirt or dress walked up the stairs, they flashed their knickers at the tables below. The girl walking up the stairs therefore gave a great view of her pink underwear, to which our wives instantly remarked on how badly the staircase was designed for women in skirts and scolded my mate and I for looking.

After a couple of drinks it was time for another round and Amy suggested that she and Charlotte go to the bar. There was a long queue at the bar downstairs so the idea was floated to try upstairs. This immediately got my heart racing at the thought of my wife climbing those stairs in her sexy short dress and showing off her knickers. Charlotte was hesitant mentioning the fact that they were both wearing short dresses and Amy responded saying it would just me and my mate who would see anything (which wasn't strictly true as there were a couple of other tables with the same view). At this point I was torn between not wanting my wife to be put on display like that and also really turned on by the thought. Amy and Charlotte looked towards my mate and I and we both made jokey "we think you should go for it" comments, both of us deliberately ignoring the fact that we weren't just going to see up our own wife's dress.

Charlotte finished the bottom of her drink and said "okay what the hell" and so they both got up and made their way to the staircase. At this point my heart was racing as I realised I was going to see up Amy's dress and my mate was about to see up my wife's. They were nonchalantly chatting as they took the first steps, the angle was shallow at this point so neither of them were revealing anything. I glanced at my mate and his eyes were glued on the girls so I looked back. At about the fourth step as Charlotte raised her foot the white lace of her knickers came into view, I glanced over to Amy who now had her white cotton knickers on full display. At the next step the views up their dresses were perfect and I was incredibly aware of the intimate view my mate now had of my wife and her knickers. As they reached the top of the stairs I turned to my mate and remarked that it had been a good show to which he joked that it was a good thing they were both wearing underwear, the subtle acknowledgement that he knew that was incredibly hot.

knickers
 

At about the fourth step as Charlotte raised her foot the white lace of her knickers came into view, I glanced over to Amy who now had her white cotton knickers on full display. At the next step the views up their dresses were perfect and I was incredibly aware of the intimate view my mate now had of my wife and her knickers.
:DI have to say both Amy and Charlotte's knickers sound just perfect :D

There have been a few times that I know for SURE that guys were looking up my wife's skirt. She used to never wear anything under her skirts and dresses, except for maybe twice in decades.

Once at a store, she got out of the car and the dude pushing carts got an eyeful of her goodies. He stopped to look. She wasn't totally pleased with him staring, but she understood why and didn't blame him.

Another time at a restaurant, she was getting out of the booth and a guy watched her get out. Again, she didn't blame him and nothing she could do about it, but it was gross seeing his burger literally fall out of his mouth.

Her own dad saw once while she was getting out of a car. He made some gross comments, too.

Sitting on a couch during a family event, trying her best not to let everyone see her blue panties. But everyone saw her blue panties and she knew it.

On the floor playing with some toddlers and inevitably her dress came up and her purple panties were exposed for quite some time, with all of the adults staring, men and women.

Minigolf on a very steep hill in a skirt so short it barely covered everything. She didn't realize how short it was until she saw vacation photos later (otherwise she wouldn't have worn it). No panties. Several people noticed and looked up longer than they realized as we worked our way down the steep hill, hole by hole.

Las Vegas
 

Story is a little long, but I think worth it!

A few summers ago, I was dating a really pretty thin blonde girl and we sent to Vegas for a weekend in July. On the first night we mainly hopped around from bar to bar then brought food back to our room to eat. On the elevator to our room I asked her to flash me so pulled down her top and bra and showed me her amazing tits but before putting them away she turned and shook them for the security camera and anyone watching it.

She being a little drunk and not wanting to get anything on her clothes decided to strip down to just her lacey purple panties. One of my close friends was texting me at this time and I had described what was happening. He made a joke about how he'd love to see that, and I told him to facetime us.

About a minute later I got a facetime call from him and I picked up. At first I had the camera pointed at me who was laying across from her. After a little, I turned the phone to her so he could see her sitting legs crossed in her panties topless on the bed. She let out a little laugh scream and covered her boobs with her arm and said hello. We talked for a few minutes, and I would switch the phone to me or her. After a while she would either move her arm up to cover her boobs too late or would not even bother. It was a great start to our trip.

The next evening we were feeling really frisky and I convinced her to wear her cute yellow sundress out without any panties. There was one couple walking behind us when we approached a grate. I looked over at her and she gave me a little smile. As she walked over the grate the back of her dress blew up completely exposing her bare ass to the couple walking behind us. The best part was hearing the woman notice and say "oh my, wow".

We continued our night roaming around and bouncing around the bars. We sat at one high top in an empty bar and when we left she spread her legs wide giving me a show as she got up. We had a great night walking around with a lot of ass grabbing and making out. Once we decided it was time to head back to the hotel we began the stroll back down the strip.

Approaching the grate, I looked around and it was now packed with people in front of us and in back of us. Our stride slowed a bit and I moved us slightly more toward crossing the center of the grate. As she stepped on the grate her dress flew up this time exposing her ass to everyone behind us and her tight bald pussy to everyone in front of us. It felt like her dress was up for such a long time but it was only a second or so as she made no effort to pull it down she let it fall naturally. I watched as one guy passing by turned his head, eyes glued to her pussy and said "Damn!". There were so many eyes looking at her pussy as we walked over that great.

So to recap, in one weekend, my friend had seen her tits, maybe a security person saw her tits, and multiple people saw her ass and pussy. Last part, a few weeks later we visited my friend and it was the three of us drinking. I was making jokes about things and her boobs. She said something another friend seeing her boobs when I let her know my friend in front of her was the one on the phone. She looked shocked and said "wait you saw my boobs?!" to which he replied yes. She turned a little red and let out a loud laugh.