I had a high school math teacher who was brilliant, the only reason the was teaching HS instead of college, was that she had just followed her husband when he transferred. She was tall for a woman, over 6', and she had zero self awareness, when she was demonstrating a math principle, she might scratch her butt or reach up high so her panties were in clear view. She had 5 shirt waist dresses that buttoned up the front, you could tell what day it was by which of the almost exact same dress she was wearing. Sometimes she didn't have the buttons straight and there were gaps, nipslips were common. Sometimes when she would put her foot up on a chair, her white cottons were on display.

The next year she didn't return, she had been awarded a large research grant and was working for NASA, not surprised.

An extremely intelligent woman (and implied nerdiness) having wardrobe malfunctions is one of the hottest scenarios there could ever be!

Two women come to mind.

First was a girl who lived in a friend’s apartment complex. During summer, they’d have a pool party every other week with a band, the beer flowed. This girl would wear a tiny bikini and dance wildly. You could count on her boobs popping out five times an hour. She’d always scream and put them away. Personally, I think she was an exhibitionist. Also, her tits were on the skinny and saggy side, so we watched her more for the comic relief.

The second was a college friend of my daughter. She wore these bras that had cups larger than her breasts allowing you to see all of her boobs if you were anywhere near her. She a nice set of Bs with great nipples. Always looked forward to seeing her.

My wife and I had a lovely friend in her forties who was particularly prone to clothing malfunctions. Alcohol was usually involved.

On one occasion, she was leaning forward towards me in a borrowed swimming costume that was soaking wet. The costume was too big for her and appeared to have lost its elasticity.

As she talked excitedly, the weight of water in the costume pulled it off her revealing her boobs and i guess pretty well everything else at the front. When I told her she was undone, she said “Oops! Sorry”, hitched the swimming custom back up and continued talking to me without missing a beat.

Within a couple of minutes, her tits fell out again so I just let her get on with it. There wasn’t much else I could do as she clearly didn’t care.

There were other friends around, but they seemed not to notice that the lady’s boobs were hanging out. Probably, they were just too polite to draw attention to them.

I could tell about more dramatic consequences of our friend’s recklessness, but that wouldn’t be fair to her and might enable people to identify us.

I was in a youth group in high school that was religion based & a lot of the members went to school with me and played sports with me . There was a friend group of girls who were very pretty . One was tall with huge muscular legs and butt from swimming (Michelle ), one was short and cute but with a soft curvy little body (Rachel ), one was athletic body preppy dressed who played tennis and wore lil skirts (Alex ) and one had freckles and was about 5’6” and skinny.and cute and did drama (Brandy ).

They were sorta reserved bc like I said this was a religious youth group but they would often prank each other in ways that would reveal their panties . The first time I observed this was when we had a dance and they wouldn’t stop flipping Alex’s skirt up so she turned it around on Brandy and they did it to her instead and I was just watching from across the dance floor captivated . Alex was wearing light blue boy shorts that maybe she considered “safety shorts “ bc she had pantylines underneath . Brandy had Victoria’s Secret granny panties with flowers . They caught me looking and giggled at me . I knew them growing up so I was friends with Brandy and acquaintances with the rest of them .

In the morning we all gathered in the banquet hall from breakfast . I saw Rachel and Michelle taking their plates up. Michelle was wearing a t shirt and baggy sweats . While she was holding her tray of food walking to her table , Rachel yanked her sweats down revealing her zebra striped panties that were a little small and showed her buttcrack and didn’t cover the bottom of her asscheeks . Michelle was surprised and embarrassed and turned red . As soon as she could put her tray down and pants up , she tried to pants Rachel , who held on to her short for dear life . Rachel managed to keep her shorts from falling completely but we could all tell she was wearing white Hanes her ways and she was bright red bc she was so shy .

So as I befriended them and got to know them , I realized some of them were less embarrassed then others . Brandy would strip to her panties just for laughs or even to just swim or change . One time she invited me to her sleepover with abt 8 of her girlfriends . I could hang out but I wasn’t allowed to sleep there which was understandable and I was happy with that . So I they were trying on clothes and Brandy was the first to change in front of everyone into pink panties with white waistband and the other girls were like “omg that boy is right there “ and she said “it’s ok I change in front of him all the time he doesn’t care” and I said “yeah “ and took my pants off and stood there in my tighty whities and all the girls kinda gawked and giggled at me . It was one of the best experiences of my life tbh lmao . They couldn’t believe I wore those bc they were not considered cool at all during this time . I tried on one of the girls school uniform with a plaid skirt . I got to see most of their undies that day it was super hot

Exciting night for us! Manage to make a perfect outfit with a loose bra and flowy dress. Both the neckline falls around the nipple area and she has full control over how much her nipple can be seen.

We chose a quiet Japanese place and ordered. The waiter was awed because he could see her right nipple everytime he served us. He probably walked past us 10 times to see her brown nips. Needless to say, i was having a hardon the entire time

Fun thread. I have a couple to add. I don’t know if they qualify as “prone” but they both involve multiple sights of the same girl.

The first is Heather, the daughter of my parent’s best friends. We all grew up pretty close. She had returned from her first year of college and we did our annual trip where we stayed at a cabin. Most days were spent at the lake and often in the evening we would use the hot tub. Apparently during her year at college Heather had blossomed in the chest area. However she was wearing the same bikini she had the year before. Her large C cup tits were a bit snug in what had to be a b cup top. No less than ten or so times did I happen to catch her areola and a couple times her full nipple as she climbed onto the dock or out of the tub. She would exit then casually adjust her top. She must’ve felt it was off kilter but not that she was exposed and furthering the exposure but adjusting it. Needless to say my teenage brain was exploding the whole weekend.

The other story is about a girl I knew at community college named Tina. I was involved in some extra curricular activities, one of which was planning and doing decorations for campus events. Tina was also in this group. She often wore short dresses. She must’ve bought them all at once. They had the same style just different colors and patterns. It was her signature look. The dress was almost like overalls on top with a blouse or t shirt underneath. Then the bottom was a thick denim material that ended about an inch or two under her butt. Early in the year I happened to be doing something behind her while she scribbled a sign together on a table in the cafeteria. She leaned way over the table and her dress rode up about a third of the way up her cheeks. She had on tight white panties (such a turn on for me). So tight and thin you could see a hint of pink skin through them. The hem rested about two inches up her cheeks so her buns showed nicely. Me and a couple guys made a habit of doing our work near her and behind her. Always a disappointment when she’d show up in pants or a longer dress. This situation with the table happened often. But the best was a time she asked me to help lift a banner. It was laid on the floor. Rather than bend down to lift it, she crouched and lost her footing and fell backward exposing her pussy mound pressed against her tight white panties. It was a quick thing but I could see the darkness of her pubes through her panties. I helped her up and gave no sign that I’d seen anything and she didn’t seem to consider that anyway. She was more embarrassed by falling. But it gave me a thrill that’s lasted over two decades.

My son has been taking swimming lessons since he was 16 months old. At that age, one of the parents has to go into the pool with the baby. One of the mothers is very prone to downblouses and has shown her breasts several times. The best part is that she is very hot. She is tall, very thin, has pale skin and a beautiful face, due to her Eastern European heritage. Her son is about the same age as mine, maybe one month diffrerence. Sometimes she would wear a bikini that would usually dig into her crack when she got out of the pool. But that is not the best part. After class, she would put on a strappy loose-fitting dress and take off her wet top. Last year, I saw her breasts a few times when she bent over to put her son in the stroller. She has medium-sized breasts with small, rosy nipples.

This year, my son and hers turned 2 and progressed to a new level, and now the kids go to the pool without their parents, supervised by a teacher. But even so, she has shown her breasts a few times. One time after school, with a strappy dress and no bra, she leaned forward to hold her son and I saw almost her entire body, both tits included. I've seen 3 downblouses scenes this year and I think I saw them 3 times last year. All with different dresses or blouses. I don't think she ever realized what I saw.

When I was a teenager, a couple of my parents' friend told me about a holiday they'd all had together. This would have been in the late sixties before toplessness became commonplace.

The guy complained that his wife's bikini top had fallen off as she climbed out of the hotel pool. From what I could gather, she'd done her best to maintain her dignity in what might have been an embarrassing situation. Admirably, she'd stayed calm despite having her tits out in front of lots of people. She just quietly recovered her top and calmly put it back on.

She said that it had been no big deal and didn't bother her at all. Her husband said that it did bother him. He hadn't wanted a bunch of Spanish waiters to see his wife's tits.

Decades later, I was with my young son in the leisure pool at a sports club. He was playing with another boy whom he'd befriended. The boy's mum, who I knew slightly, was standing poolside in her swiming costume waiting for him to finish. After a while, she told him it was time to go.

Trying to be helpful, I lifted the boy up to her. She bent forward to grab him in her arms. As she did so, the front of her costume sagged a little, giving me a close up view of her lovely boobs.

I couldn't avoid seeing them and she realised what was happening but couldn't do anything about it. For a moment she'd appeared to be embarrassed. Then she thanked me and walked away with boy.