Me and my boyfriend RP a DC AU wherein I play Jason Todd/Red Hood and Dick Grayson/Nightwing, and SpartaDog plays his OC Ian Savage/Switchblade/Edge. They're currently a polycule, with Ian dating both Dick and Jason. Anyways, that backstory aside:

This is Ashley Waylett. He's a DC fan character, born and raised in Gotham City. His mother was a drug-addicted prostitute and his father was presumably one of her johns. He was practically raised by the sex workers of Gotham, and thanks to them, when his mother died of a heroin overdose, he never had to turn tricks himself to make a living. He helped the sex workers steal from their johns and got a cut of the profit.

Jason finds Ashley around a year after his mother dies, and mistakes him for a scrawny girl in a dress. As it turns out, he's a scrawny boy in a dress. That would be image number one up there, where he's fourteen and probably loudly proclaiming "It's not a girl's dress, it's my dress, and I'm a boy!" Anyways, Jason ends up taking Ashley home with the intent of only keeping him for a couple of days while he figures out what to do with him and then he... just... never leaves. He definitely confuses his new wardens with his gender expression. Ian and Jason are sure to ask him if he feels like a woman, because hey, they'll support him no matter what, but Ashley assures them he identifies as male. He just likes wearing pretty clothes.

He gets put into a public school where he ends up having to take a lot of private classes to catch up to his peers. He finds school to be a waste of time, especially since both Ian and Jason are high school dropouts. Granted, they're also both criminals, but that doesn't mean they want him to pursue the same life path. Ashley also finds his peers to be rather... lacking. They're immature and naive, and sure they've got book smarts, but he has street smarts, and guess which he thinks is more important.

Needless to say he more or less cheats his way through school and ends up skipping as much as he can get away with. Parent/teacher conferences are quite the ordeals for Jason and Ian, and they find themselves fighting the school to allow Ashley to wear whatever the hell he wants, and fighting with Ashley to stop giving the school and teachers such a hard time. Jason ended up teaching Ashley some basic self defense to fight off any bullies that tried to pick on him for his fashion choices, which led to a whole other set of issues.

It doesn't take long for Ashley to drop the dresses, which had been hand-me-downs from the girls on the streets, and start wearing skirts and feminine shirts that he got Jason and Ian to buy him. For being a street kid, his tastes definitely ran to the expensive brand name stuff, to which Ian and Jason were skeptical about buying him. There was stuff that was similar enough that was a hell of a lot cheaper that they figured he could live with having. It was just clothing after all. Unfortunately Ashley disagreed, which led to him trying to figure out how he could acquire enough money to buy his own damn clothes.

Which led to him offering tutoring lessons, though it was more like one big study group. Except it was actually a front for a gambling ring where he hustled his peers out of their money. Most were from fairly well-off families that gave them allowances so his guilt was next to nill. It worked, for a while, but Jason eventually figured it out and Ian flipped his shit. So that put an end to that, which also put an end to Ashley being able to buy whatever fashion he wanted.

By the time he was sixteen, which would be the middle picture, he had created quite the image for himself. He'd ended up dying his hair, because he figured there were more than enough blue-eyed, black haired people in his "family", thank you very much, and he was a goddamned ~individual~. It would also be around this time that Jason and Ian would start walking in on Ashley with girls, which led to a little bit of confusion because they'd honestly assumed that he was gay. Turns out he's quite the ladies man and rather enjoys being able to share clothes and hair products and such with his girlfriends. None of his relationships last long but he's not looking to get serious anyways. He's a teenager, he just wants to have fun!

He'd also begun just flat out stealing things that he wanted. Whether it be clothes or jewelry or high heels, and whether it comes out of a store or off someone else matters little to him. If he wants something, you can be damned sure he's going to find some way to get it. Of course, he's far from perfect, and he ends up getting caught a few too many times which leads to lectures from Jason and Ian and a juvenile record.

One way or another he ends up hearing tales of Catwoman, and thinks that would be the perfect way for him to get what he wants. He could steal high profile items from rich Gothamites, and then turn around and sell them to the highest bidder so he could have cash in hand that he could then use to buy what he wanted. So he starts planning, and saving, and being a lot more careful with his money and what he steals from where. He convinces Jason and Ian to let him take self defense from a licensed teacher, and enrolls himself in a Wing Chun course. He eventually is taught how to use the butterfly swords as well, though he's by no means a master with them, or even in Wing Chun. Growing up around the Batfamily, he's picked up a few things, including toys.

Not wanting to be caught this time, he carefully constructs a new persona for his planned thieving. He takes voice training. He goes to the trans women and drag queens that he knew from his childhood to learn about padding and tucking. He works closely with a freelance designer to make him an outfit that was mostly modified military stealth armor that offered both mobility and protection, two things he knew were essential thanks to his upbringing among vigilantes and criminals. Then it was just a matter of putting it all together, temporarily coloring his hair, and heading out into the night.

It made perfect sense to him. He'd idolized women since he was a kid, and dressing up as one made him feel powerful. Anyone who thought that women were the weaker sex or who thought him weaker for chosing to be one while he stole from the rich and pretentious would be more likely to get their asses handed to them. Of course the very first person he runs into as Magpie is none other than Nightwing, the other third of Jason and Ian's polycule, and Ashley throws himself into his role. He flirts outrageously with Dick and is tickled pink when Dick flirts back, and then he manages to slip away into the night with his secret identity intact.

He's not entirely selfish. He ends up donating a lot of the money to the sex workers and homeless of Gotham. He just ensures that his closet is nicely padded first, is all. And he's definitely played hero when he's noticed people, especially women, in trouble. But for the most part he remains nothing more than a thief and the adopted kid of a crime lord and an ex-serial killer.

Of course... all of this beyond "Jason takes Ashley home to Ian" is entirely speculation because none of it has happened in RP yet. Buuuut I personally imagine it going down somewhat like this. We'll see I guess! Still a long ways away from him entering the picture but I look forward to the day he does!

Ashley Waylett, Magpie (c) Scott Francis