What jobs see the most upskirts?

[piecenick]

Not counting medical jobs. I was working for a restaurant doing valet parking in the 70's when skirts were short. About half the women under 40 that I opened the door for and helped her out, rewarded me. I'm sure mostly unintentional, but when they swung that leg out, Boom. The other valet and I were keeping score.

[Gnome72141]

I used to work at a security desk for a high-end corporation, so all women wore skirts and blazers. They would all sit down in the chairs, get out their laptops, and open their legs just enough to balance their laptops on their knees to get some work done while they waited to be brought to an office. Upskirts every day, all day, for two years.

[George VI]

Does “student” count as an occupation? I would bet that students still see more upskirts than most of us, from both other students as well as women teachers. I don’t know how many students wear skirts these days, and actually it’s been a few years since I was in a classroom even as a parent. But ten to fifteen years ago I was in high schools at parent-teacher conferences and open houses and glimpsed a few teacher opportunities. One was a young Social Studies teacher sitting across from me in a short skirt that flashed just the quickest glimpse of white panties. In another classroom, an attractive English teacher was sitting on a stool at the front of a classroom in a fairly short skirt, her thighs at eye-level to us sitting at the desks. I didn’t get the money shot that time, but I noticed a lot of the classrooms had stools up front for the teachers to sit on while lecturing.

And then I would just guess that a teacher would be a good occupation to have if you like upskirts. There still have to be some students out there that wear skirts and get sloppy with the way that they sit in class.

[Iamsailing]

IT support has to be high on the list, all that crawling around under desks..

Quite a while ago I worked in an office where the desks were laid out in large irregularly shaped blocks which lead to quite long under desk journeys whenever there was a job involving cabling with no-one at the desks really knowing where you were unless they could see you through a gap or you accidentally brushed against them.

One afternoon a guy came back reporting that one of the girls was going commando which lead to quite a lot of extra troubleshooting trips being made during the day

We always had a suspicion that she knew what was going on but we never asked.

[AliDubois]

Yup, IT works for me. I was working in an office in Germany. It was summer, hot. One of the girls was in a VERY short skirt working at a desk up against the wall. I needed to get down under the desk to alter some plugging, so rather than having her think me a perve ( I DID quite like her) I told her what I needed to do asked her if she wanted to move away for a few moments. She said "No", she was busy, and told me to just get on with it. So I did and the temptation to get glimpse up her skirt was just too great. She didn't seem to care. I suppose that's continentals for you.

[wolf86]

I worked in a furniture store for a couple years and realized you can get a lot of upskirts if you stand in the right place when women sit down/get up from couches and chairs. But the best ones come from women trying mattresses if you stand near the foot of the bed or the side, and they would often last a fairly decent amount of time. I saw plenty of underwear and bare pussy views, with a lot of them actually being nice to look at.

The most memorable was a gorgeous blonde that was probably early 20s that came in with her boyfriend. She/they must have been into exhibitionism because there is no way that almost every time she was in I got a show by accident and later she would give me this smile like she knew I enjoyed looking at her. She had a really nice fit body with full C tits and she never wore underwear. She had a delicious looking pussy with a sexy little landing strip that I got to see probably almost a dozen times. She would either wear short skirts or dresses or a couple times gym shorts that had big leg openings so when she sat right you could see straight in the leg to her pussy. One of the best views was when she had on a tight dress and laid on a mattress for a good 5 minutes. When she got on the bed it worked her dress up to just below her ass cheeks and then she would keep her legs apart enough that I could see her pussy the whole time. At one point she even raised her knees up and brought her feet back close to her ass and holy shit was that a view. I could see her entire pussy and asshole, both spread a little. Needless to say, after they left I had to go on break and rub one out haha.

[piecenick]

I do IT now and I can verify the other posters. My favorite was this woman's sportswear shop, the main PC was in this nook under the cash register. The only way to access it was to lay on my back or side on the floor in front of the register. The ladies working there had to check out customers so they would stand over or straddle me. It was a store joke "no commando, Chris is working on the PC." I'd pretend not to look up, but I'd get busted all the time.

[yellow_fever_01]

I worked at a full-service gas station and was expected to wash the windshields of the cars while the car was being gassed. This was in the late 1960s and miniskirts were still popular. I have since learned that a woman always knows exactly how much she is showing, and to whom, but back then I didn't realize that the upskirts I saw were deliberate.

[lisasmithy]

i tend to show a bit of leg in the office

[magnaebony]

Worked at a service station while in school. Had more pussy flashed at me that you can imagine. Also had a lady offer me a squeeze or suck of her bare tits for a gallon of gas, and a motorcyclist offer me a blow job from his wife for a full tank.