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.