Disclaimer: I do not own Once Upon a Time or any recognizable characters

AN: This is a prompt from dannystar9 who was my 1300th reviewer for Incoming Messages.This came from Tumblr's onceuponasnacktime's headcanon. I hope you enjoy little Henry!

Regina had control issues, anyone in town could see that. Not only that, but the Mayor was distrustful of everyone and believed that if she wanted something done right she'd have to do it herself. That motto, along with various other reasons, was why she had rejected numerous daycares claiming that a one to five ratio of adults to children was too much and would give Henry ample opportunity to hurt himself or worse. She had rejected nannies, even ones with stellar recommendations and she didn't even bother with the teenage babysitters. Only a select few were allowed to be alone with her four-year old, and even then, the time they spent was minimal.

Her paranoia was the reason why instead of investing into a daycare, she allowed a small corner in her office that was dedicated to her son. Over the years, the corner, remaining the only source of colour in the black and white room, had shifted to adapt from the baby to the toddler Henry was now. What held a small playpen turned into a rocker which eventually was scrapped all together when the boy became mobile.

Now it was Henry's office, as he liked to call it.

Just beside Regina's oak desk was a miniature wooden desk Regina had Marco construct for the boy. Mother and son had spent a messy afternoon painting it the multicoloured beauty it was now, with flecks of orange and red and green splattered everywhere, drawings of suns and trees and stick figures adorning the sides and their handprints in white on the top right corner. Henry had never been so happy when his mother had moved his desk into their office when he started school, and every day after kindergarten when Sheriff Graham dropped him off or his mother picked him up, he would place his backpack and jacket on the lowered hook on the wall behind him, retrieve his colouring book, crayons and juice and get to work.

Henry most certainly felt like a big boy. He even had his own plastic coffee mug with his name on it, but instead of the yucky coffee, he drank juice. He and his mother agreed it was healthier anyway. More often than not, one of his teddies would sit in the mini visitor's chairs in front of his desk waiting for his schedule to clear. Currently Rex the dragon was sitting patiently in the small plastic chair.

His mother would type on her computer, a big hefty thing, but not him. He liked to do things the old fashioned way. Papers littered his desk with scribbles on what needed to get done in the town and pictures of all the things he was going to add. His school would get converted into a giant jumping castle complete with a slide and a ball pit. In the middle of the park would be a landing strip for the rocket ships he had in production. He was also a part-time astronaut, but he loved his work in Storybrooke too much to devote too much attention to it. To top it all off, there'd be a candy store on every corner.

He grinned holding up his latest picture of a candy store catering specifically to chocolate and made out of chocolate. It was tough work being the Mayor, but someone had to do it. Like the rest of his designs, he filed it away safely in his drawer where the design fairy would come in during the night and keep them in file for him. He leaned back and looked to his mother, giving her a grin before toasting her with his juice mug and taking a sip.

"Hard at work, I see," Regina smiled and stood from her desk to crouch by her son. "Are the teddy citizens causing you too much trouble?"

The boy shrugged expertly. "I can do it."

Regina grinned and pressed her lips to his forehead. "I need to go meet with someone downstairs for just a little bit. I shouldn't be more than ten minutes. Can I trust you with the town while I'm gone?"

The boy nodded. "That's easy." He'd been Mayor for a full four months now.

"Amelia is right outside if you need anything. She'll check on you if I'm not back in ten minutes."

He nodded again as his mother left before taking the time to sip his juice. He was midway through putting his mug down when the Sheriff popped his head in.

"Hello Henry," he grinned stepping into the room. "Is your mother in?"

The boy put his mug down and clasped his hands over one another on his desk. "Nope. I'm here."

"Can you let her know I came by to discuss the budget with her?"

Henry pointed to the seat Rex wasn't sitting in. "Have a seat, Sheriff."

Graham narrowed his eyes in confusion. "I beg your pardon?"

"Have a seat," Henry said again.

Hesitantly, and looking around the room as if the four-year old was pulling a prank on him, Graham came to stand by Henry's desk.

"I could grab a chair-"

"Sit." The firmness in his voice held no doubt that he was Regina's son.

Awkwardly, the six-foot man attempted to maneuver himself into the plastic chair. He was already slipping off of it despite his attempt to balance. His knees were pressed to his chest, and his hands were dragging on the floor.

Henry took another sip of his juice before picking out a fresh new crayon. "What's up, Sheriff?"

Graham looked uncomfortable and confused. "Just the budget."

Henry nodded, doodling on the paper to make notes. "Right. What does budget mean?"

The Sheriff chuckled at the innocent question and the serious tone. "It's the money the Sheriff's department is allowed to have in order to get supplies and pay our staff."

"You need more money?"

"It looks that way, Henry," Graham answered.

"For what?"

Graham scratched his head. He only knew he was supposed to discuss the budget.

"Tell you what, Sheriff," Henry began. "If you can turn my school into a bounce house, I'll give you more money."

The man had to chuckle at the boy's logic before the sound of Regina clearing her throat had him tripping over himself and the chair in his haste to get up.

"Thank you for taking care of my meetings, Henry," Regina smiled at the boy who gave a look saying it was all too easy. She turned to the stumbling man. "We'll reschedule discussing the budget."

Nodding, Graham quickly exited the office.

"This is easy," Henry decided before he held up a finger signalling his mother to wait as he picked up the play phone on the corner of his desk to take a very important call.

That night when Regina put Henry to the bed, the four-year old hugged her tightly and whispered. "I want to be Mayor when I grow up."

She kissed his cheek and settled Rex beside him. "Don't grow up too fast."

He nodded sleepily before succumbing to his dreams.

While in her home study, Regina had to grin at her son's interactions with Graham earlier in the day. His expression was serious and adorable when speaking to the fully grown adult.

She has watched the entire thing hiding just behind her door until she decided to step in to spare Graham any further embarrassment. Rummaging through her briefcase, she retrieved the designs Henry had made that day and smiled fondly at each and every one of them before placing them reverently in a box labelled 'My Little Mayor'.

THE END