This is a work of fiction, inspired by a picture and caption on another site - my imagination on how the two could have gotten in the picture together.
He didn't really know exactly what he was looking for, just that he needed something that would work for the costume they were planning. So when the girl working the vintage shop asked what he was looking for Jack was honest in saying "I'm really not sure." and then they had a laugh and then they both paused and had a "Don't I know you" moment.
She figured it out first "Mr. Blake? It's Kylie Santos" She went to give him a hug so he reciprocated, even though she wasn't someone he was very close to.
"Wow, great to see you" he says, "What's it been 3, 4 years? You've certainly added to your piercings (she had them in her nose, on her lip and who knows what other places) Are you still going to school?"
She replies "Yeah, Mr. B, my mom wouldn't let me get anything until I was out of high school, and this year in the fall I'll be a junior at GSU, working on my art degree."
Knowing it's not the right place or time for the "Well that's not going to get you a job" lecture he skipped it and just said "Oh, that's great." He then proceeded to tell her what he was trying to find - something that would work for a group costume for the game "Elf Lord 8" that he and his friends were planning on making for the ComicCon in the city at the end of the month. "That's why I have the beard now, getting into character." So they both had different looks than what they were used to before, but she was still wearing the baggy sweatshirt and ripped jeans he remembered.
Her reply of "Oh, it looks great, very strong chin" seemed almost like flirting - it was tough to tell with these emo chicks, her totally black hair and almost scary make up made it a mixed message. She showed him around a few different ideas and he left with just about a full costume, but he would need a belt and a certain hat to make it complete. She told him they get deliveries of new stuff every Thursday, and if he wanted she could let him know if she saw anything that would work. He left his number with her and thanked her for all her help and went on his way, not really having a second thought about it.
That was until later that week when he got a text from a new number with pictures of a couple fancy hats and asking "would any of these work?"
He replied "Hi Kylie, I like the 3rd one, but it would need the red flair on it." He then made sure to save the number as her and she replied.
"I have a lot of fabric here and I've gotten really good at using the sewing machine to fix things around the shop - let me see what I can do." "Thanks!"
The next day she sent a pic again "done" and it looked great "Awesome, thanks so much!" he replied.
"U dont alwys have to youse capitals and punctuation, u know lol"
"Okay." He responded.
She gave him the facepalm emoji and said "Once and English teacher always an English teacher - it is the summer u know"
They then made plans for him to pick it up that Friday.
When he got to the shop, they had another nice conversation, and when he asked how much he owed she gave him her store discount - and he asked how much for the sewing she did and she said "On the house, but I do have a favor to ask" He was intrigued. She asked about the group going to ComicCon and she told him one of her art classes had been about stage make up and costuming, and she had done the make up for several people who went to a show last year, and showed him a couple pics of her work.
It was amazing - it was almost to the level of the movies and shows themselves. He complimented her work and said "Well, could we hire you to do our make up that day?"
They texted back and forth to set things up, and he kept the conversation going for a while, eventually asking if she ever cosplays herself or does she just do other's make up. Per usual she kinda downplays having done it, but eventually mentions that when she has dressed up, it's been at small shows or some clubs that do theme nights. Then she eventually does what he had been hoping for - she attaches a picture of herself dressed for one of her nights out - and he could not have been more shocked! The absolutely skin tight cut out top with her huge tits almost bursting out of it, cleavage for miles and the shortest skirt he'd ever seen - it might as well have been a belt. He had no idea those baggy tops and sweatshirt were hiding absolute monster tits, the only delay for him responding was his need to rub out a load to it immediately!
It may have been bold, but he took the next step and asked her to meet him for coffee, he knew a nice place they could hand out and not be bothered by anyone and they agreed to meet after her shift the next afternoon.
"Why don't you dress like that normally?" He asks, no point in beating around the bush - he wants to get to see her in costume!
"It's an alter ego. I go to a club once a month or so and put on a kind of one-woman show."
"I would really love to see that, a side of you that didn't show itself before."
"I would never let anyone from this backwards ass town know I was doing anything unusual, so I have a spot in a club about an hour away.
"What does the act consist of, like singing and dancing?"
"It has elements of both." She gave a smile he thought meant something deeper "I would never do anything like this myself, but when she's "acting" as 'Esmerelda' she can do just about anything. It's so empowering. " She makes him promise not to mention it to anyone, especially at her work.