What was the best job you've had for wardrobe malfunctions?
 

I've had a few that filled my spank bank, the first one that comes to mind was parking valet. I worked parking cars at a 5 star restaurant, you had to be in good shape for running to get the cars, we only got paid the tips we earned and in the summer the heat was incredible. I started working there in May of 1968, skirts were short and every car door I opened for a lady was an adventure. I saw every type of panties, pantyhose. girdles, garter belts and rarely, nothing but bush.

Sunglasses were a must, or you'd get busted staring. Some women were modest and knew how to exit a car without exposure, but about half, the skirt was too short or the car too low, and many women just didn't care, a valet was a nobody. A good night you could make $15-$20, high roller money in 1968.

Second, was deckhand on a tour dive boat, helping divers with tanks, wet suits, flippers. If a woman was wearing a bikini top, when I pulled the wet suit off, over her head, the bra was going to come with it. Usually they stand there with hands over boobs until I could untangle the bra out of the vest.

Many years later, I had to handle all of the A/V for fashion shows for upscale stores, usually crammed into a booth behind the change area. Nice.

Photo Booth error
 

I used to work in a bar a few years ago, that had a photo booth machine in it. The lay out of the place was quite unusual and the photo booth was opposite the bar itself.

Regularly you would get groups of girls go in, very drunk and take photos flashing the screen, not realising that as well as the strips that would print off. The images would also show up on the monitor on the outside of the booth.

It was crazy how often that I’d be working and look up and see a collection of tits/asses or more.

As a kid in the 70s working in a gas station was very similar. Washing windshields gave you an upskirt on the lady in the passenger seat almost every time. Women still got dressed to go out in those days and the fashion was short skirts.
From the window you very Often saw down blouse shots as they fumbled in their purse for payment.

If she was really hot you would ask her to come see something under the hood or a tire to keep an eye on. Providing more opportunities to open the door, then kneel down and speak up at her or have her lean in over the fender.

The women would often played the same game and tease us young guys the whole time as well.
Damn you self-Servs!!

Worked in a college bookstore during grad school. Helping girls search for text books, particularly on low shelves, and being across from them while they bent over to write checks. In in early 70's, with the braless age just hitting it's stride, I often had 100 braless downblouses on a busy day. Occasionally, they were totlly nude under a sundreww, and you got to see all the way down, from nipples to bush.
Plus, you had the time to chat them up, and occasionally meet them for a "better look" after working hours.
I would have worked there for free.

2 jobs I had when I was a student.

One is located in a supermarket where I sat across the cashier. In summer, many young ladies wearing short dresses or skirts coming getting groceries. I could enjoy looking at their long legs on the way in. Also when they checked out, they grabbed their items in carts, that bent down gave me good view up along the thighs, more luckier I could see up their skirts.

Another is a boba shop. Making drinks is boring, but sometimes I gotta take the post getting order. I like some girls were lazy picking up the menu but lower their head to get a good look. Making me, in front of them, had chances look down their tops. If those were blouses, U neck or V neck, I could see their bras. Furthermore, lucky to see some braless ladies, I would have maximum patience letting them take as much time as they need in front of me.

life guard

I was a bank teller while I was going to college. Back then it was nothing but women coming in and endorsing or signing checks. I got to see any number of women including a couple of classmates, one of whom I still believe did it on purpose.

I can say that I had 2 Great jobs for Oops!
 

While still in High School I worked in a GAS Station just like another Member above stated and it had some perks!
Even though the guys that worked there with me hated doing the windows on cars and the Boss expected you to do it on all the cars too!
But when there were women drivers or as a passenger, we had no shortage of guys wanting to wash the front window to see if we could get any good views and I have to say many did take advantage of showing Us plenty because they knew what we were up to!
The other job was working the New car Auto shows, we got to take care of the Models from the start and walk them around to their break room!
I can say many things about women Models, their not Shy nor Embarrassed on showing any of their Goods!
They would call us and we went one guy at a time taking them to their room! At the room we had to wait for them to get done, so being nice and polite they would ask us to step inside their room and enjoy some refreshments with them! Besides that they never wanted to dirty or wrinkle those outfits they wore, so they would request Us to help un-zip them so they could remove them and relax more natural~
I must say they went so Natural under those outfits too!
Then we had show women doing stage stuff like Magical Acts and other things! Watching them getting in and out of their outfits was great for getting a nice "bobber"!
Just like somebody else said, I would have done that Job for FREE but instead I got paid for it very well and with Extra Benefits too!
:) :p ;)

My wife told me that when we used to have attendants clean the windshield, if he was cute and she had a mini on, it was too tempting to flash her panties. She said she would even wear nicer panties for certain guys. One time we were on a trip through Oregon, at the time you were not allowed to pump your own gas, she was not wearing panties, that guy got the full monty while she pretended to read a book. Some jobs have built in benefits.

Working retail was huge for this: Women running in to get something when they had planned on staying home all day, so they come in braless, tanks with huge arm holes, bending over to see things on shelves...I saw a half dozen nipples every single day.

Being a professional musician (classical stuff, not a rock band): Seeing so many women wearing things to perform with that they had never worn before (when I used to coach musicians, I would tell them to practice in their attire before wearing it on stage, but most women didn't). I can't count how many times a woman would sit to wait, bend over, hold their instruments, etc, and the gap between their bare breasts and the dress was enough to see everything without even trying, but they didn't realize it because standing up normally didn't show anything.

It was actually pretty common for women to flash you as you cleaned the windows or give down-blouse while speaking to them through the window. They would have far more buttons open than they would normally have open just walking around. You got to know what ones were the keeners to put on a show…. They would keep you talking longer than needed as well.

Little did they know there were no pockets in those coveralls and we actually had straight access to our hardening dicks when we had our hands in the pocket holes… lol

I Saw a lot of hard little nipples in those days.
As a horny teen it kept you up at night…

I was a supermarket delivery driver for a while and I remember delivering to a teacher during the holidays. It was my first drop and she was wearing shorts and a really loose tank top. When she bent over to pick the shopping out of the crates I got a perfect view of her small pale boobs and pink nipples. I think she must have been aware but I enjoyed the view. I had another customer who was old and fat and she definitely showed them off deliberately, the 2nd time I visited she wore a cardigan with nothing underneath and her nipples visibly got erect as she was bending over slowly lifting her shopping

Greenhouse
 

A couple of years I worked part time at a large family run greenhouse. At first I just took the job so I could qualify for early departure from my high school class day.

I soon discovered it was a gold mine for down blouse voyeurism.

The greenhouse was managed by the wife of the owner who had bought the business for her to operate.

Their two teenage daughters worked there too.

The mom was actually more attractive to watch because of her large breasts.

The four of us worked side by side each day in the hot environment getting the plants set up on the low display tables.

Their usual attire was low cut Tees or halters, most often bra less. I can still visualize every detail of mom and her daughter’s sweet breasts.

Then there were the countless numbers of female customers that as my job was to show them around.

My favorite customers were the wives who let me see what only their husbands got the privilege to see. Great memories!!

My first job while still in high school was as a car hop at an A&W drive in restaurant. The owner employed guys as car hops because he thought guys were harder working. Standing at the drivers open window to take orders, taking trays to the cars, or picking trays up from cars, gave me a great view of the driver and front seat passenger. Depending what a female driver was wearing, I got to look down at boobs and cleavage all day long. Skirts were were riding high up as she sat behind the wheel and legs were on display all the time. Women in the front passenger seat would often turn in their seat to face the driver and me standing at the window. Once again, skirts would be riding high up their legs and I could often see panties. I'm sorry to say I never did see any bare pussy.

One Summer during college I worked at a kinkos as a delivery driver. I mostly delivered boxes of copier paper, or bulk print orders (like a box full of flyers or whatever). There was one office where I made deliveries once or twice a week, and I would leave the order with the receptionist and wait while she proofed the delivery. She was a couple of years older than me, maybe 23-25, not the prettiest, but she had a nice body. Every time I delivered I would get a downblouse shot of her. It never gaped, so no free nipple, but a couple of times I caught her wearing a bra that I could barely see through. It wasn't much, but it always made the day better. Tried flirting with her, but failed miserably.

Nuclear Security Officer
 

One of my duties as an armed security officer at a nuclear power plant was to observe people entering the facility. Most people don't realize that when entering, all packages are x-rayed and personnel have to pass through a metal detector and explosive detector. The metal detector was no big deal but the explosive detector was.

Personnel explosive detectors work because nozzles blow consecutive jets of air upwards at you in quick succession as you stand there, hands at your sides, starting at your feet, then your legs, hips, chest and finally your head. That causes molecules to become dislodged from your body and rise up where they are trapped and analyzed.

Most women who entered wore dresses and regulars knew what to expect and held their arms tight to their sides, hems held tight. On the other hand, new employees, summer interns and visitors had no idea what was about to happen until they were caught in the classic Marilyn Monroe on the Subway Grate pose! You could depend on it happening half a dozen times every day. Even regulars coming back from lunch could get distracted and forget until it was too late and that was the grand prize because every time I saw them later in the day, I'd smile at them and they'd get embarrassed all over again, lol.

Over the 20 years I worked there, I lost track of how many panties and thongs I saw!

Swap Meet Booth
 

My high school job in the’70s was working for a guy who refurbished and sold guitars at a swap meet. There were many braless gals in those days and they would lean down to look at the cheap ones that we set on a blanket, or the better ones that were on guitar stands. I saw plenty of bare breasts and lots of bras downblouse.
Some would try out a guitar, sitting on one of the chairs we had. They would hold the guitar in their lap and prop one breast up on the waist of the instrument while strumming.
Sadly, there weren’t very many upskirt opportunities, most of the girls wore either jeans, shorts or hippie maxi-skirts.

I've had 2 of the best jobs
 

When I was younger I worked as a Carney running carnival rides. The best ride I ran was called the Zipper, the tubs spun around as the boom turned. If the women wore loose tops, tube tops, skirts or dresses, they were falling down or coming up. I could make the tubs spin so fast that they had to hold on to the bars & left themselves exposed the whole ride. Plus the benefits of what some women would do for a free ride. Kiddie rides were full of down blouses when the mothers lifted their little ones outta the carts.

Drove semi truck for over 30 years, people have no idea how much you can see looking down into those cars as they go by. You name it, I have seen it going down the road, women love getting dressed going down the road. I don't know what it is about women that they love putting on their pantyhose in cars going down the road. Or the women who love putting their feet on the dash wearing short skirts. Used to get flashed by women all the time back in the 80's & 90's, not so much anymore.

Beach workers
 

Here in Europe people working on beaches may see a lot of topless, thongs and sexy wardrobe malfunctions.
My wife and me always go to the same beach near our house and there is a guy working as lifeguard but also taking beach umbrellas and loungers to the customers. He has been working there for more than ten years.
Ten years ago every day he could see about 10 topless, 10 thongs, 20 nipslips/oops and 100 bikini.
Recently women habits have changed, less topless more thongs, so 3 topless, 30 thongs per day.
I am sure because this is what I see on the same beach.
During the last ten years my wife has been one of his "preys".
She is a prude, no topless, no thong, but she suffered more than 50 sexy accidents including nipslips (my wife in the second photo, it is not one of the best but it is the only one I have in photo) and oops (first photo, not my wife taken from the web).
She had also two major sexy accidents.
First one: She was standing in the middle of the beach and her bra fell on the ground (a failure of the clasp). She was surprised (taken off-guard) and she remained topless in front of him (and many other guys) topless for more than two minutes before resuming the bra. Everybody was looking at her because she was screaming.
Second one: she was touched by a jelly fish on a thigh very close to the vagina. I ask to the guy a first aid support, he arrives with a spray and without any hesitation he starts to rub the thigh of my wife almost touching her pussy. My wife was suffering and without any care she lifted and shifted the bikini bottom exposing her pussy. The guy had her pussy at few inches from his nose.
I believe that this guy is the one who has seen more nudes of my wife

Women's Shoe Store
 

One of my male friends works as a saleman in a women's shoe store. What a sissy job, eh.

Six Flags Log Ride
 

I was a ride assistant at the Six Flags Log Flume ride. It was dark in a portion of the ride, and we had to have an attendant in the dark portion of the ride in case of some mechanical breakdown or accident. However, there was a light on in a narrow portion of that dark area that allowed us to check on the riders. The sections of the log carried two people per section. Girls would sit in the front with guys behind them. Many of the guys would get a pretty good feel off their girlfriends during the ride since the girls were almost sitting on their laps. Often, the couples thought it was dark enough that no one could see anything. As they passed under that one light, I could see pretty well. Guys would have their hands down the girls' tops or have their girl's jugs pulled out completely as they massaged their boobs. Sometimes the girls would realize they had been exposed and other times they didn't realize it and business continued as usual. It was a nice gig!

Technical support
 

I worked in technical support which meant spending time crawling about under desks sorting out computer and cabling issues, I use to go to call centres full of women and it really was running the gauntlet as the engineers were fair game for the women to try embarrass us , loads of down blouse and upskirt views . While sitting at desks and women leaning over to get somethings or while I explained something or training them. Some were very touchy feely as they knew we couldn't say anything as the women would just turn it back on us to be our fault.

There was so many times I would see right down their tops, some never seemed to ever wear bras and I know some didn't wear knickers , we would always ask the women to move if we had to work under the desks but sometimes they would just say it was ok and to carry on and I did get the usually line of while you are down there. They use to do theme days to elevate the boredom of the job so they would all choose to dress they same way, some days were knee high boots days , others days were high heels and short skirts. During hot summers they would do swimwear days and the company laid on BBQ's and pools ,other days were fancy dress. Halloween and Christmas were always the best. It was a fun place to work but temptation was really high and I did go out with quite a few of the women which could be even more dangerous as they women would talk about it all

Since it was a 24/7 environment we use to work shifts and the night shift was the most risky as it was also the quietest and most boring so things did go on. We just had to be so careful as is was instant dismissal if anything was considered inappropriate .

Women's Shoe Store
 

I've actually been inside the store a couple of times to see my friend in action. First he would pick out a couple of pairs of shoes and help the woman put them on. He would be at feet level and look north (see pic).

At Disney with my ex-wife on that space tram thing in Tomorrowland, it broke down and we were stuck in a dark part of the track, and someone on the loud-speaker said "to all of those stuck in the dark, we have cameras and can see you," and we knew it was because people messed around in the dark, and yes, my ex-wife and I were going to try to do as much as we could while it was broken down until the person on the loudspeaker started speaking (I think I had already had her boobs out of her top by then)!!

Riverboat Drink Server
 

For a few years in college I was a drink server on a riverboat. If it was already a windy day, women would dress usually accordingly. But if it was sunny and there was no wind when people stepped outside their houses, women would have a tendency to wear lighter skirts that are prone to the wind-aided upskirts.

Being on the river alone will have natural gusts of wind to it that are stronger than when you just step outside your house. And the riverboat is also cruising 15-20 miles per hour itself. But from my experience it was the random gusts of wind that would usually catch women in skirts off-guard.

In my three years working as a riverboat drink server, I saw so my wind-aided upskirts that I lost count. Usually just a little buttcheek or panty flash. A full "Marilyn Monroe" never happened that I saw. But many girl's butts in their underwear. The best was when it would happen to an older mature woman, but those sightings were rare. Girls in their 20s though it happened often.

Hospital
 

I worked construction in a number of hospitals and female doctors and nurses were always unaware of their under wear showing through or under their scrubs. I remember one little blond in particular that could never quite keep her bottoms on tight or she would wear light colored scrubs with dark panties

I always thought the old school shoe salesman would have been the ticket. You have all the upskirt opportunities while
Fitting and the angled mirrors and the down blouse as they bent over to admire or fiddle
With the new shoes. I expected to hear from them here - it was on my radar as a kid but never had a chance to work ina shoe store.

Bartender
 

I had a buddy who was a bartender in the late 80’s and he was always seeing upskirt or down blouses. I was helping on a particular busy night and he stopped me and a milf about 30 was doing everything she could to capture his attention. He says do you want to see up her skirt? Gives her a nod and she smiles leans back and showed us her panties. He walks over and whispered in her ear, she leaves for a few minutes, comes back and hands him something. He yells at me again, this time she spreads her legs and no panties.

Red light district cafe
 

When I was 15 I got a part time job in a small cafe in the city centre (50 years ago)
At the time I didnt know, but the area was very near the red light district and the cafe was frequented by the ladies of the night.
The ladies state of dress was usually very tight and ultra short mini skirts and I often saw a bare bum or hairy pussy.
Similarly with their low cut tops or see through blouses I saw plenty of boob.
The ladies weren't particularly good looking and many were over weight. They took great pleasure in teasing and flashing a very red faced young lad with a permanent boner however.

I was only there for a couple if weeks but still have fond memories.