A Girly Confidence Boost (GP Quicky) (Patreon)

A Girly Confidence Boost

Although it’s just Zeke and Izzy in the room, he still feels completely exposed and very uncomfortable.

“You look nervous…,” Izzy says, giving him a wry smile. “I don’t bite. I promise.”

Zeke nervously smiles back, before looking down at the towel clinging to his waste. He points at the maid’s uniform and accessories sitting on the small changing table to Izzy’s side.

“I am nervous,” Zeke says plainly. “I’m standing almost naked in a room with a girl I’ve only just met. Can we get this over with already?”

Izzy brings a single hand to her mouth as she giggles. “We’re friends now though, right? I mean, I did just shave your legs, chest, and armpits. I did your makeup too, that makes us friends in my book.”

Going bright red at the fact he’s now hairless all over, he scoffs. “Do friends nominate each other to do extremely embarrassing things in front of the entire school?”

“Yes,” Izzy snaps back with a playful smile. “It’s called having fun!”

Zeke shifts uncomfortably on the spot for a second before making a snarky comment. “Why me though? Why do I have to be a maid this year?”

Izzy waves away his protests with a single hand. “Cos you’re the cutest boy in our class and we all want to win this year.”

Zeke grumbles under his breath. “It’s because I’m short and skinnier than the other boys, isn’t it?”

Picking up the bright red bra that Zeke is to wear, Izzy gives him the biggest grin as she holds it up in front of him.

Neither of them moves as Izzy waits for him to take the bra from her hands. Zeke waits for an answer to his questions.

“Well?” he says, narrowing his gaze directly at her. “It is because I’m scrawny, right?”

“I never said that!” Izzy replies innocently, as she stares right back at him. “I told you. It’s because you’re the cutest boy in the school and we want to win!”

Zeke quickly looks away in frustration. “That’s you telling me I’m more girly than I am handsome. I’m ugly.”

“Fine,” Izzy huffs, thrusting the bra into his hands. “If you think you’re ugly, then be ugly. But I will not have this lack of self-belief in yourself ruin the beauty pageant for the class. Please, just get dressed.”

Zeke snatches the bra from her hands and dangles it around his face. He looks at it momentarily like it’s the hardest math question he’s ever encountered.

“Seriously?” Izzy sighs. “It’s a bra. It’s not rocket science.”

Izzy instantly snatches the bra back and opens the cups and straps. She signals for Zeke to put his arms into the straps like he’s a child being taught for the first time. Quickly moving around him, as the straps rest on his shoulders, she does up the clasp.

“That’s not too tight?” she asks, looking at him with a satisfied grin.

“No, it’s fine,” Zeke answers reluctantly.

Playfully snapping at one of the straps, Zeke looks down at the matching panties waiting for him on the table.

“Whose underwear is this?” he asks curiously.

“Mine,” Izzy answers, reaching for the panties. “I promise I don’t mind you wearing them. The bra doesn’t fit me anymore anyways. I’ve grown out of that cup size.”

“Oh,” Zeke replies, looking at the empty cups of the bra adorning his chest.

Izzy wafts the red briefs in front of Zeke’s eyes to get his attention. “Slide these on underneath your towel and get comfortable in them. You’ll be wearing these for the rest of the school day, so make sure you don’t pull them up too tight and crush your bits.”

Taking the panties from her hands, Zeke awkwardly and carefully slides the panties up each leg, still clutching the towel for dear life.

“Good!” Izzy grins as Zeke eventually stands, looking slightly more uncomfortable now that he’s wearing her panties. “Now for the tights, suspenders, and dress.”

Izzy looks at Zeke and feels for him for a second. He looks so uncomfortable, but she knows in her heart that he will win and it’s just the confidence booster he needs.

“You ready,” She grins.

Zeke bites his lip and looks at the frilly black maid’s costume. The nervous get the better of him and all he can muster is a simple nod.

As much as Zeke complains about the feminine outfit and attire, Izzy quickly gets him suited and booted into the costume. The dress sits wonderfully on his shoulders and cascades down his body with grace. His legs, encased in sheer tights, look surprisingly elegant.

“How does it feel here?” Izzy asks, adjusting the fit around his stomach. “I’ve done it tighter to cinch in your waistline. It’s not too tight, is it?”

Blushing like a ripe tomato, Zeke looks down at himself wearing the frilly black dress. Frowning for a moment, he doesn’t want to admit to her that it feels great and is surprisingly soft and comfortable.

“It’s fine,” he says, not knowing how to hold himself when wearing a dress.

Izzy takes a step back from him. Intently looking him up and down, she takes in every detail of his transformation into a young maid girl. She studies his light, but natural make. She adjusts and tightens his ponytail.

Feeling like he’s being dressed by his mom, Zeke admits to himself that he can’t help but enjoy the attention shown to him by Izzy. Usually, no one really notices him.

“Confident?” Izzy asks, breaking the calm silence between them.

“Sorry?” Zeke asks, awkwardly brushing hair from his face.

“The heels,” Izzy clarifies. “Are you confident with them? Do they fit ok?”

“I guess so….”

“Good, good. Can you give me a twirl and a cute pose?”

Zeke raises an eyebrow and gives her a stupid look. “Twirl? Pose?”

“Yeah!” Izzy giggles, flicking her hair with confidence, then giving Zeke a peace sign with her fingers. “Enjoy yourself!”

Zeke attempts to copy Izzy and instantly blushes and goes shy. “This is silly,” he grunts.

“Why?”

“Cos…,” Zeke mumbles, turning away. “I’m ugly and look stupid.”

Annoyed, Izzy puts her hands on her hips and fiercely frowns in his direction “Are you joking with me right now!?”

She points at his face. “Cute little button nose, but beautiful lips and cheekbones I’m jealous of!

Moving to his chest, she points again. “Adorable little figure with not an ounce of fat on you!”

Wafting up the skirt of his dress, she giggles. “You look adorable right now, Zeke. If I hear you say you’re ugly one more time, I’m going to smack your cute little tushy so hard!”

“Y-yeah…?” Zeke asks, unsure of himself.

“Oh, deffo!” Izzy replies passionately. “So cute! Please, just do me one favor!”

“What’s that?”

“Please enjoy yourself!” Izzy says, putting her hands together like she’s praying. “Allow yourself to be pretty. To be feminine! Enjoy the feeling of long hair and a sexy little outfit tight against your body. Enjoy the spotlight for once. Let people lust over your perfect little tushy. Let the boys drool over you as you walk in your heels. Just have fun!”

Looking pressured, Zeke forces himself to smile. “I’ll do my best!”

“Thanks, cutie,” Izzy says softly, giving Zeke a gentle peck on the cheeks. “I know your will!”

As the beauty pageant starts, all the other nominated boys from the other classes stand up on stage. One by one, they introduce themselves as the characters they’ve dressed as. Some of the boys have cross-dressed, like Zeke, but others are characters in fiction.

As Zeke is called up onto the stage, he’s terrified. He’s the last to introduce himself and he’s by far the most tense.

Izzy, standing at the front of the school crowd, jumps up and cheers at the top of her lungs! “Go, Zeke! She cheers! “Cutest boy in school!”

Focusing solely on Izzy, instead of the crowded school auditorium, Zeke feels a confidence he’s never felt before. He feels supported, wanted, and finally part of something

“Go Zeke!” another girl screams. “Show those dumb boys it’s ok to be pretty.”

The school auditorium starts to bounce as the kids start clapping for Zeke. The support from the school almost brings Zeke to tears as he gives everyone the widest smile.

Giving a cheeky pose, Zeke pulls the same peace sign as Izzy did earlier. The school goes wild!

“Cutie! Cutie!” They chant.

As the winner of the contest is called, the entire school cheers. Zeke is crowned!

As he struts off the stage with newfound confidence, the boys in the school surrounded him, desperate for his attention. They’re all after selfies and pictures with the newest cute maid in school.

Unable to stop himself from being swept away by all the attention, Zeke starts milking it and acts like a teen idol. He glows with feminine confidence and grace.

Proud, Izzy stands back from the crowds and smiles. She knows she’s made a new friend for life. She knew he had that confidence in him all along!