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

AN: It's been a while since I've posted a Growing Up series oneshot, and I've had this prompt from let-myloveopenthedoor for a while. Prompt: Henry's first haircut. Hope you guys enjoy!

Regina Mills, Mayor of Storybrooke and Evil Queen of the Enchanted Forest, feared by all and tested by none, had one weakness, and it came in the form of a two foot tall boy with a mop of brown hair on his head and a temper that rivaled her own whenever he saw a pair of scissors near his head.

Henry was generally an even-tempered child, waving to everyone on the street as Regina pushed him around in his stroller yet always trying to escape the confines of his stroller whenever Pongo was near. More than once Regina caught the 18-month old trying to climb the Dalmatian. While Regina would eventually muse upon the fact that Henry was becoming a little knight in training with his noble steed, there was no stopping the harsh lecture she had yelled at Archie for not keeping a more watchful eye on Pongo as she lifted Henry from off his sides. Other than that, Henry was a little angel, excluding his temper tantrums and his constant need to fight bedtime, but Regina loved him just the same.

Though Regina's patience with the little angel in disguise was wearing thin as he clung frantically to her leg, refusing to let go even as she walked up to Raquel, Storybrooke's hair stylist who specialized in children's haircuts.

It was Henry's first haircut, and though there had been many attempts in the past to cut his hair before, now, with his mess of brown locks scraping his shoulders and his bangs covering his eyes, Regina refused to let his cries or his pout distract her from getting the job done.

She was reluctant at first to come to Raquel's. Regina's incessant need to control everything and her overprotective attitude had her first attempt to snip her son's hair to be in the comfort of their own home, Henry seated in his high chair and a bowl on his head. He had giggled at the silliness of the bowl, wobbling his head from side to side and trying his best to look up to catch a glimpse of the moving plastic, but as soon as he caught sight of the barber's scissors, he froze up instantly.

It was probably due to Regina's constant reminder to Henry that sharp objects, knives, scissors, letter openers, pencils alike, were off limits to him, and it was most likely why he went into a fit upon seeing the dangerous object so close to his eyes, wielded by his mother no less. He had fidgeted so much, the bowl had fell off his head and it was impossible for Regina to get a strand of hair without nicking her panicking son.

It was a week after that when Regina decided to take Henry to Raquel's. His eyes had widened at the colour inside the shop, vibrant greens, yellows, and reds, and instead of chairs there was a rocket ship, a horse, a train, and a chameleon, the children's favourite with many of the regular customers dubbing him Pascal. Despite Regina's disdain for everyone in town, she gave credit to the young girl who had a knack for calming children and unruly hair alike if her own train of blonde hair that drifted down her back was anything to go by. She relaxed when Henry had lifted his arms up to be put on the horse, nudging its sides and hopping up and down as he pretended to gallop. Regina grinned with a steadying hand on his back as they awaited their turn. By the time Raquel had come by, Regina was already thinking of all the errands that had to get done for the day, but Henry had caught sight of the scissors and all but leaped from the horse into his mother's unsuspecting arms crying "No! No!"

It took Regina nearly an hour to calm him down, but by then she had refused the blonde's service and opted to take Henry home.

Now, with their fifth visit to Raquel's and Henry's bangs causing him to walk into objects, Henry had learned that this colourful little shop was a place of horrors, and Regina had to pry his hands away from her legs, groaning about the fact that his nails, which needed to be trimmed just as much as his hair, tore her stocking.

"Henry," Regina soothed as she gathered the year and a half old into her arms. She moved his bangs out of his face and ducked to catch his eye, making a point that his hugs would not get him out of this visit. "You need a haircut or mommy can't see your beautiful little eyes."

He pouted and removed his arms from around her neck, crossing them around his chest in defiance. "No."

She rued the day Henry learned that word and hated the very likely probability that he had learned it from her as he sat in on her meetings.

"It's not up for discussion, young man," she scolded as they made their way to the hairdresser who smiled despite the numerous times the Mills had walked in and out of her establishment.

"Ready to try again, Henry?" Raquel asked the boy who cowered into his mother. She patted his back before turning her head to address Regina. "Think we can get him to cooperate this time?"

"Perhaps if he takes to you this time," Regina sneered as she followed the girl to the chameleon chair this time. All the other chairs had proved useless, but perhaps this one would be lucky.

Similar to the horse, Regina placed, at least she attempted to, Henry onto the green amphibian, but he refused to let go of the collar of her dress. "No! Mama! No!"

"Henry," Regina sighed aggravated. "We talked about this. The scissors will not hurt you. I promise you they won't."

He remained unconvinced as he clung to her despite still sitting on Pascal.

"Why don't you sit with him?" Raquel suggested.

"I beg your pardon?"

"He'll feel safer if you're there with him." The hairdresser ducked her head to speak with Henry. "Will you feel better if your mommy sits on Pascal with you?"

Henry nodded furiously into Regina's neck, his fists tightening around her blouse collar.

"Very well," Regina sighed and sat sideways on the porcelain chair. It was uncomfortable and awkward having to maintain her balance and keep a firm hold on Henry as he sat facing the mirror, and just like every other time, Henry squirmed as soon as he saw the scissors.

Regina held her hand up to pause the girl from doing any cutting and slid off the chameleon, a hand still keeping Henry steady. Giving the shop a quick glance to confirm that they were the only customers, Regina slid her leg over the chameleon chair, mindful of the skirt of her dress, and kept her hands firmly on Henry's waist from behind.

All it took was a simple glare to Raquel to get the softening smile and the 'awww' on her lips off of her mind at the sight of the Mayor sitting on a porcelain Pascal in a child's hair salon holding her frightened son. A quick glance at the mirror had her cringing at such a state, but she noticed with great pride that Henry had stopped his fidgeting and was relaxing into her touch.

Raquel held open the style cape, but Henry shook his head furiously knowing that once that weird dress was on him the scissors were going to come out. Regina tucked one hand around Henry's waist and used the other to ask for the cape. She shook it out in front of him, balancing him between her as she held it out with both hands. "Look, Henry. It's just like what Superman wears, but instead of just on the back, you'll be protected everywhere."

Henry eyed it curiously, extending his hand to touch the material before tugging it toward him. Regina draped it around his body, tucking the styling collar into it before clasping the velcro shut.

"Let's get this over with," Regina said to Raquel before leaning down to whisper softly into Henry's ear. "You are being a very good boy."

He beamed up at her, but as soon as he caught sight of the scissors he froze. It took a kiss to his head and a soothing hand running circles on his back to get Henry to remain perfectly still as Raquel took the first snip.

"Looking more handsome already," she grinned, placing the first cut into a baggy. She grabbed a Polaroid from a nearby station and held it up to her face. She snapped a picture before mother and son could realize what she was doing, and by the time the picture was printing, she had already set the camera down. "A little souvenir everyone gets for their first haircut."

She fought the urge to yell at the girl for taking her picture without her permission, seated on a lizard out of all things, but it was Henry's shy smile that pulled her thoughts away. She gave him an affectionate squeeze, pleased when his smile turned into a genuine one before Raquel continued to cut. After fifteen minutes of trimming his bangs and cutting his hair to cling to the nape of his neck rather than his shoulders, Raquel stood back with her hands on her hips. "All done!"

Henry climbed up Pascal and used his mother's help to stand and look at himself in the mirror.

"There's my handsome boy," Regina beamed, helping to remove the cape from around his neck and brushing off any strands of hair that may have fallen through. "That didn't hurt now, did it?"

He shook his head and ran his fingers through his hair, amazed when the hair didn't slide through them like before. She scooted off the chair gracefully, her years of riding perfecting her technique, and helped Henry to the ground, holding his hand tightly when he attempted to play with the clipped hair on the floor.

After Raquel rang them up, she handed over a certificate clipped to the baggy of Henry's first hair clipping and the Polaroid picture. "Congratulations on your first haircut, Henry." She said handing the package to Regina but beaming at the little boy. "Maybe I'll see you again next time?"

Regina didn't bother to look at the picture, hoping to get rid of any evidence that she had been sitting on some little toy chair, as she took Henry's hand and tugged him toward the exit. He waved shyly, following his mother's brisk steps.

It was when Regina had put Henry to bed that night, her fingers weaving through his freshly cut hair that she looked at the certificate she had left on his bedside table with the picture of them sitting on Pascal, Regina holding the boy protectively as he leaned back into her, her lips pressed against his ear whispering soothing words of encouragement. She smiled softly at the image. Perhaps it wasn't such a bad thing that Regina had sat with her son for his first haircut. It wasn't that embarrassing of a picture even with the obvious run in her stocking and the awkward positioning of her legs as she straddled the chair. Henry was so obviously curled into her despite his fear, and it tug fiercely on Regina's heartstrings. She pressed her lips to his forehead and brought the certificate package with her into her room.

She dug through her closet to pull out a scrapbook, bypassing Henry's very first pictures coming home and his first steps and his tiny inked hand and footprints to find empty pages. She took extra care to paste the certificate into its pages as she glued the picture and Henry's first cut lock onto the complementary page. She dated the top of the page and in cursive wrote 'Henry's first haircut.' With her gaze focused on the picture, her smile grew more and more as she continued to stare. Motherhood had its difficulties, that much Regina knew, but feeling the contentment and the safety radiating from that picture had her realizing just how worth it, it truly was.