My Gender Holiday Part 2 (Story Mode Reward Story) (Patreon)

So I'm starting to get back into the swing of things now. Hopefully more content to share soon :)

Here's the next part of 'My Gender Holiday' as reward for being a Story Mode Supporter. Thank you so much for continuing to believe in me Nin. :)

We pick up with Trent (having just had his hair and makeup done. Enjoy

Part 2

Standing in front of Isabell in just a towel, Trent blushes as his sister points a finger at him.

“Did you shave all over?” she questions, wagging said finger as she looks him up and down.

Trent bites his lip. “I did,” he replies, itching his chest. “Now my skin is all sore and red!”

Isabell’s eyes light up and she can’t help but let out a small laugh. Looking at the hack job her brother has done with his chest, she can only assume his legs are the same.

“Here,” she smiles, holding up a small tube of moisturizer. “This should help.”

Holding his towel up around his waist with one hand, he grabs the tube with the other. “Thanks.”

Holding the tube in one hand, Trent just stares expectantly as Isabell dumbly smiles back. She doesn’t get the hint at all.

“Sis,” Trent says bluntly. “Do you wanna turn around or something. I don’t want you to watch me apply this while I’m naked.”

“Oh,” she giggles, promptly turning around. “Sorry. It’s just with the outfits I’ve found for you, I’d almost forgotten there that you aren’t a girl.”

Having allowed his towel to drop around his ankles, Trent sighs as he applies the moisturizer to his sore skin. “How could you forget I’m not a girl…?” he asks, a little annoyed.

Listening to her brother slap on her expensive moisturizer, Isabell frowns. “Sorry..,” she replies back sarcastically. “It’s not every day I choose what undies of mine my brother can wear. I guess it made it easier to think you were one of my girlfriends.”

“What ‘undies’ have you chosen?” Trent asks reluctantly, spreading the moisturizer across his razor burnt skin.

Isabell smirks and wonders if she should tease him. “Well….,” she replies.

“I’m not wearing a thong!” Trent quickly interrupts. “Don’t even try me with that!”

“Why not!?” Isabell teases annoyed that he’s said no.

Turning around to confront him, they catch each other's eyes and both of them go bright red. Isabell forgot he’s naked!

“Izzie!” Trent shrieks, covering himself.

Nervously giggling, Isabell swiftly turns back to look at the wall. “Sorry! I forgot again!”

“Forgot I’m a boy!?” Trent questions, terrified of the answer.

“No,” Isabell laughs. “Forgot you were naked.”

Shaking his head at his sister's stupidity, Trent closes the cap of the product and throws it on the bed. Reaching for his towel, he pulls it up and covers himself. His skin feels so much smoother and soothed. He’s thankful she shared.

“I’m done,” Trent says, with a lack of excitement in his voice.

“Good. Can I turn around now?”

“Yup.”

“Feel better?” Isabell asks curiously.

“A little,” Trent replies, touching the sorest spot on his forearm. “Am I really going to have to shave all holiday?”

“Yup,” Isabell replies, mimicking him from seconds earlier.

“Stop enjoying this so much,” Trent whines.

Grinning wide, Isabell tucks hair behind one ear as she looks down at the bed at the items she’s selected. She picks up a small pair of soft-looking black briefs. Holding them up towards Trent, Isabell watches him blush.

“Nothing to get all shy about,” Isabell giggles, allowing him to take the briefs from her hand. “It’s just cloth at the end of the day.”

“Easy for you to say,” Trent replies sarcastically, holding up his sister’s briefs. “Imagine if you had to wear my boxers. Would you still have such a satisfied expression on your face?”

“I guess not,” Isabell sighs. Grasping the matching bra, Isabell again grins wide and holds it up to Trent. “Still, I’m letting you wear some of my favorite stuff, so please don’t ruin them! Remember, women’s clothes are delicate—so please be careful!”

Semi-listening, Trent again stares at Isabell wanting privacy. Eventually, Isabell understands. Pointing down at the red halter-neck dress on the bed, Isabell then checks the time on her phone.

“The zip is on the side,” she explains. “It should fit you—seeing as we are similar sizes, but please be gentle with it. If you’re going to be a woman for the next few weeks—you’ve gotta be so gentle and refined.”

Trent just nods as Isabell leaves the room. As she closes the door, she tells Trent not to take too long. Reluctantly, Trent slides the briefs up and gets comfortable. They are a little tight but super soft. He then, with a great deal of difficulty, hooks up the matching bra he’s been given.

“Argh…,” Trent grumbles, pinging a strap of the bra as it digs into his shoulder. “I don’t see why this is needed.”

Itching around his chest around the empty bra cups, Trent reaches for the dress and holds it out in front of himself. He’s no idea where to even start putting it on. Seems to have holes in every direction.

He tries once and gets frustrated. He tries again and finds the hole too small for his head. He tries a third time and starts getting a little angry.

“Izzie!?” Trent groans, calling out for help. “I can’t get this stupid dress on!”

Seconds later, much to Trent’s embarrassment, Isabell opens the door and peaks inside. Trent shy’s away, covering his manhood tucked away in her panties.

“You ok?” Isabell asks, trying not to giggle at the fact she’s seeing her brother in a bra for the first time.

“No,” Trent sulks. “I can’t get this on!”

“Are you joking!?” Isabell laughs, pushing the door wide open. Entering the room, she walks over to him and bonks him playfully on the head. “What are you…like five or something. Your head goes in the head hole!”

Trent frowns and holds out the dress that’s now mangled and inside out.

“I told you to be careful with my stuff,” Isabell says, snatching the dress. “I can’t believe I’m having to help you get into this. I’m supposed to be doing my makeup right now!”

“Sorry,” Trent replies childishly. “It’s not like I asked to wear this one. I would have been happy with skinny jeans and a hoody.”

“You can’t wear a hoody out for dinner,” Isabell scoffs, concentrating on the dress in her hands. “You’ll look so out of place when Mom and I are wearing dresses.”

“Just hurry up then, Izzie,” Trent moans, folding his arms. “I’m getting cold.”

“Wait a second!” Isabell says as her face lights up. “We haven’t stuffed your bra yet!”

“Huh?”

“Yeah, socks should do the job nicely.”

“Socks?”

“Sure! When I was younger I used to stuff my bra all the time. Thick winter socks were my favorite!” Isabell grins. “I’m not sure I’ve got any of those, but I’ve got some you can stick in those empty cups for now.”

“For…… now?” Trent asks, watching his sister pull out a couple of pairs of her bright and colorful socks.

“Yeah,” Isabell replies with a smile, stuffing each of Trent’s bra cups full. “Mom and I were just talking. We’d be happy to buy you some forms. Breasts can be extremely affirming for women. We’d love to give you confidence of your very own. Just what a budding young woman needs!”

“This is getting out of hand,” Trent nervously laughs, rolling his eyes.

Eventually, Isabell sorts the dress and helps her brother into it. As she pulls it over his sock-enhanced boobs, she adjusts the fit around his hips. Pulling the dress down tight, she’s impressed as to how well it actually fits him

“You’ve erm….,” Isabell comments, brushing down any creases in the dress as she circles him. “Got a really nice figure, Trent. Do you tone your legs and ass?”

Trent turns up his nose at the notion. “No.”

“Oh,” Isabell replies. Standing to his side. “Ok, deep breath in. I’m going to zip you up.”

Trent doesn’t even get the chance to breathe in. Isabell slides the zip up with no issues. The dress clings tight around Trent’s slightly broader male chest, but it still looks like it was made for him.

“Knew it!” Isabell celebrates! “Fits you so so so well! I’ve got so many friends that would be jealous of you right now!”

“Why?” Trent asks curiously.

“Cos.”

“Cos what?”

“Cos you’re a certified cutey!” Isabell torments, playfully poking at one of Trent’s sock boobs.

“You just called your brother cute!” Trent replies, thinking he’s being witty

“Brother!?” Isabell laughs, theatrically throwing her head back. “Get used to this Trent. You ain't my brother right now. Girl—you my pretty little sister!”

Trent lowers his head as Isabell claps with excitement.

“Mom!” Isabelly then cries out. “Come check Trent out!”

Feeling his entire body tense up, Trent waits anxiously. Moments later, Erin appears in the doorway. Now standing taller in her high heels, their mom has a face of makeup and looks incredible in her tight strapless dress.

“Mom…!” Isabell reacts in awe. “You look amazing! Like…ten years younger!”

“Thanks, Iz,” Erin smiles, acting all coy with a flick of her hair.

Quickly Erin then turns her attention to her son. She looks at him with his styled hair, natural makeup, and bright red halter-neck dress. Her mouth falls open and her eyes begin to water.

“Trent…,” Erin says with emotion, fanning her eyes. “You look so pretty.”

She steps closer to him and takes his hands into hers. Trent goes bright red as she looks deep into his eyes.

“You look….,” Erin gushes but then pauses to steady her resolve. “Just like me at your age!”

“I do?” Trent asks, instantly looking away with embarrassment.

“We always thought you looked more like me than your dad,” Erin continues, bringing up a hand to touch Trent’s smooth cheeks. “I was so right….!”

“Heels?” Erin asks, turning to face Isabell.

Prompted by her mother, Isabell starts looking around her room for the heels she’s unpacked for Trent to wear. Finding them, she holds the black stiletto in the air in triumph.

“Trent,” Erin starts to instruct as Isabell hands her the heels. “Now, don’t be afraid of wearing these. They might look uncomfortable, but they really do take you from cute to sexy.”

She hands a single shoe to Trent and looks down at his feet. Talking hold, Trent perches himself on the side of Isabell’s holiday bed and begins to slide it on.

“Do you remember the first time you wore heels Izz?” Erin asks, getting all sentimental.

“Yeah,” Isabell grins. “You let me wear some when I dressed up as a princess that Halloween.”

“Was so cute!” Erin gushes, handing the other shoe to Trent. “Now both my children are going to have that experience. Isn’t that wonderful Trent?”

“Sure, Mom,” Trent answers, sliding the second shoe on.

He looks down at the glossy black heels and he’s surprised at how comfortable they feel around his toes. He was expecting his feet to be crushed.

Holding out her hands to help him onto his feet, Erin gives him the biggest smile. “Up you come!”

Wobbling as he stands in heels for the first time, both Erin and Isabell clap when he regains his balance.

“Adda girl!” Erin cheers.

Gently letting go as Trent appears to get more confident, Erin leans in. “Heel-toe—heel-toe,” she says.

“Huh?” Trent ask.

“When you walk,” Erin explains. “Heel first, then toe. Heel-toe—heel-toe.”

Trent contemplates that for a moment. His mind keeps swinging back to the same question. How did he find himself wearing his sister's dress!?

“Lee!?” Mom screeches without warning, causing both Isabell and Trent to flinch.

As Trent’s father appears in the doorway, he gives Trent a cheeky smile. “Ladies, hello,” he says, acting suave.

“Don’t you think Trent looks like me when we first met?” Erin asks, showcasing Trent like a gameshow assistant showing off first prize.

“Yeah,” Lee nods, agreeing with his wife. “Kinda mind-blowing.”

Lee steps into the room. He’s wearing a posh shirt and very well-ironed chinos. The smell of his aftershave was evident.

“How do you feel, Trent?” Lee asks curiously.

“Fine,” Trent replies, unable to look his dad in the eyes.

Isabell throws her hand up in excitement, interrupting. “She needs a name!” Isabell motions, referring to Trent.

“She does!” Erin agrees, bouncing with excitement.

“How about Arielea?” Lee says confidently, almost like he’s already thought about i.

“That was fast,” Erin comments in suspicion. “Why Arielea?”

“That’s what I wanted to call Trent if he was a girl,” Lee replies, reacting innocently to the suspicion on his wife's face. “Just thought it’s a really cute name and would fit our new daughter well.

“Sure…..,” Erin says, narrowing her eyes.

“What do you think Trent?” Isabell asks, touching her brother's side. “Do you like it?”

Trent mills it over in his mind. He can feel the pressure of all of them staring at him. This was not what he was expecting of this holiday at all! Does he really wanna spend the entire trip being called Arielea?

“Ermm…,” Trent mumbles, unsure If he should be excited or sad.

Feeling extremely nervous about all the staring, he comes out with a solution. “C-can I think about it over dinner?” he asks, nervously rubbing his forearm.

“Oh shit….dinner!” Isabell squeaks in panic. “I’m still not dressed yet!”

Fumbling as she moves between them all, Isabell looks desperately at the clothes strewn around the room. She’s spent so much time selecting for Trent, she’s forgotten to choose for herself.

“Guys,” she says, stressing out. “Can you all get out so I can get dressed now!”

“Fine, fine,” Lee and Erin say simultaneously.

Trent says nothing. He just concentrates on taking his first steps. Reaching the doorway, he holds out for the frame like he’s skating on ice. Erin then grabs his arm for support.

They share a smile as Erin helps him out into the corridor. Walking together, Erin gives Trent the biggest smile.

“I’m proud of you,” she says with glee in her eyes.

“You are?” Trent asks, overthinking each and every step.

“Yes,” Erin says gently. “So proud. You could have moaned and whined about all of this, yet you’ve taken it all in your stride.”

Erin giggles and nudges Trent as they walk. “Welcome to the family Arielea! I cant tell you're going to fit in.”