I'm not sure how many of us are posting stories about working in shoe stores but here is my contribution.  

When I was in community college in IL, I worked at the local mall at a shoe store.  It was a local chain (50-ish mile radius - didn't stretch to Chicago) named after the owner's daughter.  The owner was kind of an overbearing guy who we were pretty sure was having an affair with one of our co-workers.  The store manager had been there for something like 30 years.  He was a petite man.  Every year when we were able to order shoes for ourselves at a steep discount, he ordered the size 6 1/2 zip-up Florsheim chukka boots that he wore with his dark colored double knit polyester pants pulled up a good 4 inches past his waist.  He was a decent guy but no longer had any passion for the job.  He forbade us to sell shoes to the local flamboyant jackass lawyer who was representing a dentist accused of raping women while they were under.  The lawyer was rumored to have been busted for cocaine*.  The two were all over the news and when the lawyer showed up to represent his client in a limo with a dozen roses, that just chapped my bosses ass so much that he wanted to kill the man.  But all he had the power to do was withhold his shoes.   So, this fat greasy lawyer would come in and we basically had to tell him every single shoe he wanted was unavailable.  Even the ones for his poor little girl who didn't ask to have a slimy bastard for a father.  I'm not a very aggressive person so it took a long time for me to get to the point where he said to me "ok, I see what's going on here" and walked out.  With his sad little girl in her white frilly dress purchased on credit that would never get paid off.  

 But this isn't about him.  It's about the time I lost my retail innocence.  

A guy came in to the athletic shoe side of the store.  We had two entrances; the women's/kids side and the athletic shoe side.  He obviously belonged in the athletic shoe side because he was wearing those jogging shorts.  You know the ones.  They are not for wearing in public.  He had those old man legs, the kind that are super tan but not muscular because the skin is all loose and wrinkly.  I'm not even certain he fancied himself "athletic".  It was just an outfit for him.  His wife was with him but quickly left to "head over to Bergners".   I found myself to be the only one on the floor so thus began the small talk.  He asked shoe-related questions.  He was curious if this one would provide enough support.  These looked kind of narrow.  The questions were all perfectly reasonable.  Now that I think about it, perhaps too perfect.  Rehearsed, even.   But I got him the shoes in his size and came out to do the sit down/try on schtick.  First ones, no good.  Second ones, wanted a 1/2 size larger.  The vibe was weird but I was just there to sell shoes.  Got the 1/2 size larger, sat down on the stool/foot ramp, put the shoe down for him to try on, looked up to see what his face had to say about the fit.  But as I looked up, my eyes VERY BRIEFLY hit on everything in my field of vision from the foot ramp up to the face.  It's amazing what your subconscious can pick up in the tiniest moment of time.  By the time I got to his face, this had gone on:

eew, this guys legs are so loose, why is he so tan, do old men go to tanning beds, it's like a hot dog that sat in the bathtub too long, ick old man thighs, purple polyester, PENIS!!!!!, polo shirt, did I just see his penis, polo collar, yes, that was his penis, what the fuck, chin, how do I look at this guy, he wanted me to see it, eew, eew, eew, eye contact.  

 Fuck.  He knows that I know.  I saw his purple-pink shiny uncircumcised  penis and he is the happiest he's been all week.  You fucking asshole!

"So, how do they feel?"

"These still feel a little narrow but now a little long."

"Are there any others you'd like to try?"

 "No, I'd better not, my wife is expecting me to meet up with her"

 You ASSHOLE!!!  But his wife took off in that "I'll leave you two alone now" way so she's the asshole too.  

 He leaves and all my co-workers suddenly re-appear.  Obviously, they had all had him before and that's why it turned into Death Valley when he walked in.  So, I had my first exhibitionist.  He was creepy but really pretty pitiful.  I'm sorry for whatever psychological whatnot brought him to my chair.  He may not even have been the worst person I ever helped but he was the most memorable.   Not as bad as the guy who pulled up out in front of my register at the garden center and jacked off, but still not something I want to see again.  

*  I just looked up the lawyer and I think I found him.  He's got a bunch of arrests in FL for cocaine sales, posession, resisting arrest, grand theft auto, and numerous other drug-related stuff.  Hmm.