I Can't Make This Stuff Up

During my first week of working at the shop, I was working in the shoe department and heard a man asking me if we carried this cute little pump (a woman's shoe with a short heel) with a large bow in a size 11. I told him that everything we had was out and as I started to continue with what I was doing, I noticed the pumps he was wearing, a similar pump, also with a large bow. Good chance in a size 11.

Today he came back in while I was working. He was dressed in black dress Capri's (women's slacks where the length ends somewhere between the knee and mid calf), a silk lavender blouse and black 3 inch heeled sandals. He had his toe and finger nails painted a gorgeous lavender that matched his blouse, and he carried a black purse under one arm. He was returning a watch that he said didn't keep the correct time and wanted to exchange it, but we didn't have another one like it, so he decided to just exchange it in a purchase of other pieces. He shopped for a while, carefully examining every thing he picked up. After awhile, he asked to try on a couple of skirts, a pair of slacks and two blouses. My manager made sure there weren't any women in the dressing room and opened a door for him. She and I were both near the dressing room, behind the counter when he came out in a pair of black striped slacks and asked me "Do you think they fit me like they should here" with his hand targeting his crotch area as if he were Vanna White.

Okay, I'm rarely at a loss for words, and I wasn't at a loss for them at this time either. Everything in me wanted to say 'no, they weren't meant to fit a man's penis'...but I just looked at him for a few seconds as he kept waving his hand in front of his crotch. Then, he pulls up his shirt to reveal his very large pot belly hanging over the waist band (hip band on him) and said "I'm just not sure they fit right here", again waving his hand to keep my attention where I really didn't want to look. I honestly thought for a minute, there has to be a camera around here somewhere. I told the man to turn around and he did. So obedient, this one. Anyway, I told him the only truth I could give him. I said "They make your butt look great."
There's a truth to be told about any outfit on someone: that color flatters your skin tone, that's a great color for your hair (or eyes), those slacks make your legs look longer (c'mon petites, y'all know what I mean)...there is always something, and the truth was, his butt did look pretty good in those slacks. Would have even looked better from a distance, but he stayed put. Each of our dressing rooms have at least one mirror and a triple mirror outside of the 'stalls'. Why did he need me to tell him whether the material draped nicely over his penis or not?
Apparently there is a shop rule about this type of thing. One of the store's associates has to wait inside of the dressing room area if we have a man trying on clothes, so that other women (which a couple of women opted to wait) may try on clothes without being afraid they'd walk out to see a semi-dressed...guy.

It ended up being a rather large sale, with his explaining how he thought men would love wearing this fabulous material next to their skin if they'd just give it a try, how men are missing out simply because they're afraid of what people would think of them. I didn't have to, but I did tell him that his asking me if I thought the slacks fitted him in the crotch was putting me in a rather awkward position, because I hadn't known how to answer him. I told him that it would be impossible for them to fit him the way they were intended because they weren't intended to fit around a penis. He looked at me with a little smile and said that what he'd meant was, did they pucker at the pockets, because sometimes slacks will do that if they don't fit right. I said "Darlin', it wasn't your pockets you were directing my attention to". That left him speechless while he blushed and when my manager started laughing, so did we. He then said he just loves shopping at our store and he'll be back.

Great.