Jack's Story Part 4 (Top Tier Reward) (Patreon)

Jack finds himself part of the Sonya crew!

I'm a little under the weather, so let me know if this is not good. Also, couldn't think of a name for Jack's feminine side, so leave some suggestions :P

Jack’s Story Part 4

My blood pressure is through the roof, but their smiles don’t match the looks of disgust I’d expect. Why aren’t they teasing me?

“Kid…,” Lara says, standing over me and Nathan. “What’s your stance on my ex-Barry?”

“Lara!” Nathan complains, getting up to stand beside her. “We should give him a moment to process all this before giving him the Spanish inquisition. Trust me, getting caught is very stressful.”

Hoping she’d stop glaring at me, I give Lara a very quick glance.

“Eek,” I squeak as she continues to stare down at me.

“We need to know if he’s going to rat us all out,” Lara insists. “We can’t have this one running off to tell Barry we are in here before we swap uniforms. I doubt Matt could take on a whole gang even if he claims to be a Kung foo master.”

“I…hate…. Barry,” I mutter, seething internally at the mention of his name.

“Great!” Lara laughs, flippantly stepping away. “He’s a dick…right?”

That’s when I feel Nathan place a hand on my shoulder. I look up to see his big pretty eyes looking deep into mine.

“Hey,” he says softly with a big, beautiful smile. “You don’t have to be nervous around us. I cross-dress too.”

Expecting that to be a teasing joke, he doesn’t laugh. He just holds a big friendly smile.

“Y-you…,” I point, quickly looking at the two girls to make sure they weren’t laughing. “Cross-dress?”

“Yup!” he replies confidently. “My fem side is called Sonya.”

My mouth falls open and I gasp. “You are being serious?” I ask, unable to stop a smile.

“Yeah,” Nathan giggles, turning to face Jade and then Lara. “Lara and Jade are both great allies.”

“You came out to them both!?” I gasp again, knowing how hard that would be for me.

Nathan scratches his head and goes red.

“Nah…,” he nervously chuckles. “I pretended to be my best friend’s girlfriend. It’s a long story”

“Yeah, don’t worry,” Jade exclaims, bouncing on the spot. “Your secret is safe with us!”

“Are you sure about that, Jade,” Lara sneers

Focusing solely on Nathan, I feel kinda safe in his presence.

“T-thanks…,” I reply. “I thought for a moment there, my life was going to be over!”

Nathan lets go of my shoulder and steps away. I get up off the floor and allow my dress to bellow out around me. They all start looking at me again as I stand in my princess dress.

“What’s with the costume?” Jade asks, lurching towards me. “You wanna be a princess?”

“Oh erm…,” I reply anxiously rubbing at my arm. “I want to audition for some of the girl parts in the school play. I thought I’d come practice wearing the dress and heels and stuff.

“Make sense,” Jade replies with a grin. “Hey, do you want to help us with something!? I’ve just come up with a brilliant idea!”

“Jade,” Lara whines. “We shouldn’t get him involved. That’s not fair.”

Jade starts waving away Lara’s protests. “Think about it! The more girls that are in our group as we leave…the less likely we are to get attacked. Makes perfect sense!”

I scrunch up my face confused. What is she talking about?

“Yeah!” Nathan reacts, pointing at my discarded uniform on the floor. “Jack can wear Jade’s uniform and I will wear Lara’s.”

There’s silence for a moment as I try and understand what on earth is happening! Jade’s going to give me her uniform…. why!?

“If that’s ok with you Jack?” Nathan asks, making me blush as I again gaze at his cute smile.

That sounds extremely exciting! I’d actually get the chance to wear a female school uniform! My heart screams yes, but my head is saying hell no!

“Why though?” I ask Nathan. “I don’t understand.”

Nathan spends the next few minutes detailing exactly what's been happening. From Matt walking in on him cross-dressing, to the fight earlier this morning. I’m stunned by it all! I honestly thought I was the only femboy in school, yet here we are.

I’m not alone….

“So, you going to help?” Jade grins, unbuttoning the top button of her blouse.

“Yeah!” I answer passionately. “Of course, I’m going to!”

“Excellent!” Jade cheers.

Looking across the costume room, I see the wig box in the corner of the room. I strut over to it confidently and pull a few of the wigs out.

“Nathan,” I call out, holding a long blonde wig up. “Is Sonya a brunette or a blonde?”

“Brunette!” he answers, wandering over. “Or maybe darker.”

As we both select a wig of our liking, Lara beacons Nathan into a secluded corner of the room. Jade then takes hold of my hand and pulls me into the other corner, where a screen can separate us.

“Right,” Jade declares, letting go of my hand to point at the dress I’m still wearing. “Off with that, while I go fetch your uniform.”

Unzipping the dress, I listen to Jade gather up my stuff from the floor. As I remove the heavy dress, it falls from my shoulders into a pile around my feet.

“Oh!” Jade squeaks uncomfortably, as I turn around to see her nervously looking away from my almost naked body. Only wearing the underwear I’d borrowed from my mom, I try and cover-up, but I go extremely red.

“Sorry! I wasn’t expecting you to get undressed so quickly!” Jade screeches, moving quickly to the other side of the screen. “I guess you won’t be needing to borrow my bra.”

Feeling like a complete idiot, I step out of the dress and pick it up. I loved wearing it! I can’t wait to audition!

Hanging it up on a nearby hook, Jade starts throwing stuff over the screen separating us.

A pair of white girl’s shoes come bounding over and almost hit me in the face.

“Sorry!” Jade laughs. “I hope they didn’t hit you!”

“Almost did,” I respond, picking them up to check the size.

Looking inside her shoes, we are the same size. That’s lucky.

“Socks in coming!” Jade shouts as she launches them over the barrier.

Rushing, I gather them up and slide both onto my feet. Pulling them up to just below my knees another garment comes flying over the screen.

“Skirt!” Jade chuckles.

Reaching up, I grab it before it falls to the floor. It’s still warm.

Thumbling with it as I try and work out what’s the back and what’s the front, I pull it on and zip it up.

It’s a little loose on my narrow hips.

“Hey, Jade….” I call out, not sure how high to wear it. “Should the skirt sit on my hips or around my belly button?”

“Erm…,” she replies, fumbling around behind the screen. “I wear just over my hips. Up to you though really…. I don’t have to worry about a certain something being too visible, do I.”

Adjusting it…. several times, I finally settle on a good height.

“It’s a lot shorter than I’m used to…,” I say, feeling rather exposed between my legs.

“Oh yeah…?” Jade shouts back. “If you’re worried, just try and keep your legs together!”

Doing as she suggests, I bring my thighs together. It feels a little awkward and uncomfortable.

“Blouse and top,” Jade shouts, throwing them over.

I catch them and again, the blouse is still warm. I can smell the sweet-smelling deodorant she’s used this morning.

Putting the blouse on, I grumble at the annoying backward buttons. Eventually getting them fastened, I pull it down and find her blouse shorter than my shirt. It’s tight around my stomach too.

Although, that tight feeling kinda makes me excited. It’s giving me such a feminine silhouette.

Seconds later, I’m completely dressed in Jade’s uniform. It’s very different, but I like it!

“Pockets!” Jade cheers, coming around from the other side. “You don’t know how much I’d give for the girl’s uniform to have more pockets.”

Jade struts in front of me in my uniform. It fits her extremely well and It doesn’t look at all out of place. It looks almost normal. Must be annoying for the girls of this school to have to wear skirts. Must get cold in the winter.

“Maybe we should suggest a gender swap day,” Jade jokes, getting comfortable in my uniform pants. “I’d love for all the boys in school to understand the inconvenience the skirts can be sometimes”

Jade grins and looks me up and down.

“Well, well….!” she cheekily smiles. “My uniform fits you well Jack. Look at those lovely legs of yours—I’m a little jealous!”

“Yeah?” I ask, looking down at my bare legs. “Good thing I shaved…huh?”

“Maneater alert!” Jade teases, giving me a playful grin. “You better leave some of the boys for the rest of us…ok!”

Blushing, I smirk at her comment and look away.

“Ok then, I guess Lara and Nathan are taking their time about this….,” Jade comments impatiently. “Why don’t we style your hair and do some makeup while we wait?”

Picking up the wig, I roll the cap over my natural hair, only to find heavy resistance.

This is the first time I’ve worn a wig and it’s not really working out for me. Darn, I wish my hair was a little longer. If only I’d asked for extensions for my birthday.

“Need some help?” Jade asks, standing in front of me with a silly expression.

As we both struggle to get it seated correctly on my head, eventually we flatten my puffy hair enough to get it looking somewhat realistic.

Telling me to sit on a nearby trunk, Jade finds a hairbrush and starts brushing the wig out straight.

“Y’know…,” she casually chats, running the brush down slowly. “Do you ever wonder what it would be like to be the opposite sex?”

“All the time,” I reply, winching as she pulls at the wig tight.

“Oh?” Jade responds with a curious tone. “Do you think your life would be easier as a girl?”

“Not sure. I’d be more comfortable in my own skin I guess.”

“Can I ask you something?”

“Yeah?” I reply, as she again pulls at the wig with the brush.

“When you dress as a girl, are you attracted to boys?”

“Why are you asking?” I answer, reluctant to share such information with someone I’ve just met.

“It’s my brother,” She whispers, leaning closer to me. “I’m worried about him. He’s head over heels in love with Nathan, but I’m not sure Nathan’s into boys.”

“I can see why he likes Nathan,” I reply, thinking of his friendly smile.

“Does dressing as a girl make you like boys?” Jade asks, curiously. “I think that’s what Matt’s banking on.”

“I dunno….,” I answer, getting cut off as Lara and Nathan reappear with fanfare.

“Check it out!” Lara laughs, presenting Nathan. “Look just how cute Sonya is right now!”

I turn to see Nathan completely transformed! He looks incredible and it makes me a little jealous!

“Wow,” Jade gasps. “Look at you too, Lara. Guy’s pants are comfy…. right?”

“Yeah. Pockets…. kinda useful,”

“Looking cute Jack,” Nathan grins, coming to stand next to me. “These skirts are pretty short, huh?”

“Rather revealing, aren’t they,” I reply, now even more jealous of how curvy Nathan is.

He even looks like he’s got a little feminine chest. I want that too!

“Are you wearing a padded bra?” I ask Nathan, feeling envious.

“I don’t think so,” Nathan smirks. “Lara, is this a padded bra?”

“No,” Lara replies, looking confused. “Why would I wear date night underwear to school?”

“It’s just…,” I answer, pointing at Nathan’s budding chest.

“Oh…,” Lara giggles, “Did Lara not suggest stuffing socks into your bra? We used to do that all the time when we were younger. Do you remember Jade?”

Jade smiles. “Yeah, I do remember that.”

“So…,” I interrupt, desperate to get myself looking that little bit more girly. “Should I stuff then?”

“You should,” Lara chuckles. “Will give you some feminine confidence.”

Looking a Nathan as he nods in agreement, I start looking around for some chunky socks to stuff into my bra. For some reason, it’s important to me to have a bigger-looking chest than him.

Strutting confidently away from the group, I see a pair. As I go to grab them, that’s when the costume room door swings open and a male figure appears.

Almost bricking myself, I stumble backward.

“Guys!” Moans the person whom I assume must be Matt. “Hurry up already! It’ll be night-time soon!”

Matt looks directly at very confused. “Who’s this!?” he complains, pointing at me.

Here’s my chance to finally introduce myself as a girl.

“Hiya,” I giggle, flicking my hair playfully. “I’m……..