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.