The Good Kind of Scoundrel - Carmen Sandiego

Gray x OC
Set Post Season 4

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Penny Taylor's life is the opposite of easy.

Ever since she and her little sister were orphaned three years ago, she's been doing whatever she can to get them both by. Even if that means dabbling in some petty crime every once in a while. However, when a charming regular at the cafe she waitresses at catches her attempting to pickpocket him, things start to get messy. Penny expects him to report her scam to the manager and get her fired - or worse: arrested - but he doesn't. Instead, Gray Calloway smiles his cocky smile and tells her exactly what she did wrong.

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None of the characters or world belong to me aside from Penny, Speedy, and Sam(possibly more). This is a work of FICTION. DO NOT PLAGIARIZE. I work hard on my stories. For any shippers who're considering reading this, I'm not sure if Carmen will really be part of the plot, but there will be some Platonic Redcrackle.

Credit to @MonsieurDuke for the cover.