A/N: Beta is femphoenix. :D Hope you enjoy. So happy to be writing again.

Prompt onceuponasnacktime's headcannon: Before Henry was tall enough to ride the rides at the fair Regina would give him $10 dollars to play the games. He could barely see over the counters but he'd try his hardest and one time he won a kazoo, but he wanted the dragon stuffed animal. At the end of the night he admitted defeat and he walked hand in hand with Regina back to the car. Claiming she had forgotten something, Regina buckled him in before running back into the fair. Minutes later she came walking up to the car with the grand prize dragon stuffed animal for her boy. Henry slept with his arms around it every night for weeks, claiming that it protected him from boogie-monsters.

The Dragon Fair

Henry tugged at his mother's hand which hung just beside his head. Dressed in jeans which seemed to be a miniature version of his brunette's mother and a black batman shirt, the little boy hopped forward eagerly as the flashing lights of the fair grew brighter and brighter.

"Come on, mommy. Come on," his voice took on a higher pitch in his excitement. Henry couldn't seem to stand still long, his eyes darting side to side as he tried to take in all the stands and sounds and smells.

Regina smiled softly at the boys excitement, "Henry, dear." She waited as her little son turned, a smile stretched wide across his face. His eyes didn't settle on her for long before they were back to darting to the sights behind her. The Mayor chuckled at how he fidgeted as if, if he didn't move soon, he would explode from all the energy that he was trying to keep in. She dug into her purse before pulling out a crisp ten dollar.

Henry's eyes snapped back to his mother as the money was waved in front of his face, "Is that for me?" To the little boy it was if his mommy was giving him enough money for the world; he could buy all the Batman comics in the world with that. Regina nodded with a gentle smile, "This is for you to play the games with, darling. Which would you like to play?"

The little boy was hopping in a circle trying to pick a stall that had the best prizes when his eyes landed on a large plush dragon at a stand with what looked to be three targets and baskets of beanie bags. "That one, mommy!" His hand shook in excitement as he pointed at the brightly colored setup, his gaze never leaving the dragon.

Regina held his other hand as Henry led her to the game; she eyed the game figuring he would be able to at least make one shot with the ten dollars. Even if his head barely reached the top of the counter. His mother laughed at the sight of Henry on his tippy toes, hands holding on the soft edge. The bill was placed on the felt counter before the bored looking teenager scooped it up. The Mayor looked down at her little boy and noticed his gaze hadn't shifted. Her eyes followed his line of sight to a purple and green dragon hanging in the 'Large Prize' section. She looked at the game and realized for her son to win it he would need to sink three of the beanies in the farthest target.

The game runner handed her the change that she was due and Henry five beanies. The five year old scrambled onto the provided stool, his tongue poking out of the side of his mouth in concentration. His small hand clutched the first sac and lobbed it towards the tilted targets. Both mother and son watched as it landed to the left of the first hole and slid down to the grass beneath it.

"You can do it, Henry," Regina encouraged him. The boys face a mask of concentration as he nodded sharply to his mother. He faced back to the game, tiny fingers gripping cloth and filling.

After four more throws her little boy had come close but missed all his shots. Henry looked undeterred though proclaiming that he would win next time.

The pair had returned to the stand with the bored looking teen three more times during the night between walking and eating corn dogs, the latter being a treat to the five year old.

Each time, Henry had come close even managing to sink one of his shots with which he won a small plastic kazoo. He had looked so excited until the high schooler had pulled out a tub and told him to pick a neon colored noise maker.

Regina's heart had hurt at the crestfallen look on her son's face as they walked away for the final time. It was nearly seven and the older kids and adults were starting to filter into the tiny fair signaling to the parent's of younger children that it was time to leave.

Henry looked up at his mother with tears in his eyes, "I didn't get it, mommy. I tried really, really hard and I didn't get it." His sneakered feet drug against the grass and mud, his mother not reprimanding him such was his sorrow.

"I know, baby. You did very well." The two had reached the Mayor's Mercedes and the lights blinked twice as it was unlocked. Suddenly Regina knelt down in front of Henry and stated clearly, "You know what, darling. I forgot something in the fair. I'm going to buckle you up and lock the car, okay? Mommy will be right back." The little boy nodded forlornly and crawled into his booster seat, raising his arms as his mother strapped him in. She dropped a kiss on his light brown hair and whispered, "Be back, my dear boy."

The door closed and two beeps were heard as the locks engaged. The boy watched as his mother's silhouette moved farther away.

Henry's head had started to droop when the lights came on in the car as his mother returned. Her door opened and in slid the Mayor. The boy was more focused on the object in his mommy's hands than the fact that she was back.

"You got it!" he squealed happily. His tiny arms wrapped around the plush toy's neck as he hugged it close. "Thank you, mommy! Thank you."

His bright smile and happy sigh made the extra time and money worth it for Regina. She would do so much more if it meant her son always stayed happy.

With a soft smile, the Mayor turned in her seat before starting the car and driving home, listening to the happy hum of her little boy drifting from the back seat.

For weeks after the fair, Henry refused to sleep without the purple and green dragon, which he affectionately named James, tucked in beside him. Whenever Regina came in to kiss him goodnight he demanded she kiss the dragon too.

When she asked why once he simply claimed, "He protects me from boogey-monsters just like you."

A/N: Tell me what you think please?