I worked at a place that sold body jewelry, one day a pretty gross looking woman asked for nipple rings but didn't know what size it was. I told her what size they were usually pierced with as I opened the case for her. I suddenly smelled something foul and looked up at her, she had her floppy, sweaty tit out of her shirt asking me if I was sure the piercing was that gauge.
This comes from my time as an assistant manager at "Popular Copy." I was working open to close by myself on an extremely rainy Sunday in TX. The power was out so I was sitting just outside the door reading a book, obviously not able to complete any of the work since it's hard to check email, make copies or print when you don't have power. A customer walks up to the door and says "I need to use the copiers to make a couple of copies and then send a fax." I replied "The power's out." The customer proceeds to walk past me into a dark store, attempt to use the copier and then ask why it doesn't work.
I used to work at a video store, it was my first job. We had a "back room" with adult videos you could rent. Back then it was big old VHS tapes. Anyway, this guy would come in EVERY DAY and rent 4 movies and return them the next day. When he got the movies he always asked for them to be "double bagged". A few years later I got a job at a roast beef sandwich chain down the block and this SOB would come in there, with his movies and order 16 beef and cheddars. WTF was that guy up to?
I work in a fast food restaurant and one day a kid was putting a bag of grease into the garbage and the bag ripped and this poor son of a bitch was drenched head to toe in day old hamburger and bacon grease, he shouted that some had gotten in his mouth. I never saw him again.
During the summers after my sophomore and junior years of college, I worked at the front desk of a hotel. The hotel's restaurant had a hostess who was, I would guess, in her early 70's. She was a nice enough lady and may have been reasonably attractive in her day, but apparently never realized that she was old enough to be my grandmother. She would sometimes make comments about how handsome she thought I was or whatever, which was awkward, but overall pretty harmless. One day, I had to go deal with a problem on higher floor, so I get in the elevator. She also gets in, along with the bartender whose best days are also behind her, to deliver room service. After the door closes, she said "Mike, you're very lucky; you get to share an elevator with two older women." As I'm standing there legitimately creeped out (as was the bartender), she then topped the awkwardness of her previous statement by grabbing my arm and saying "and one of them's experienced!"
So I used to work at a local Ice Cream shop here in Austin. We had a combo called the "Mint Snow Ball". A customer came in and could not grasp the idea that although the combo had snow in the name, it was made out of ice cream, not snow! She asked me what it was made out of. I told her. She asked if it was made of snow, I said it was ice cream with different stuff mixed in (oreos to look like dirt, etc) This went back and forth a few times before I finally told her, "WELL ITS NOT MADE OF SNOW!"
I work as an on-call sales clerk at a well-known department store, and the other day I was assigned to work in the woman's plus-size department because the girl who usually worked there called in sick. I can see why, given the number of morbidly obese women I had to assist in the fitting rooms (so much back fat!). About halfway through my nine-hour shift, one of the store managers came over to inform me about a customer complaint. Apparently a woman who was shopping there complained to management that I should be fired. The reasoning? I'm apparently too skinny to work in the plus-size department, as I can't understand the "special needs" of the "differently-bodied". I wasn't fired over it, but thanks to that lady for the compliment, I guess.