Gray's Mistake (Top Tier Patreon Reward)

Holding my hand over my eyes to cover the lunchtime sunshine, I spot him at the other end of the school field. I’d sat next to him in math class all last year and I’d grown quite fond of him!

“Are you going to ask him to prom then Gary?” Kev whispers, nudging me in the back.

Nervously rubbing my hands together, I turn to face him.

“Do you…..think I should…?” I whisper back, feeling my heart beating faster

Kevin furrows his brow and slowly nods his head. His expression would suggest he thinks I’m an idiot.

“But what if he says no!” I blurt out, instantly regretting my loud voice as I look around at everyone staring at me.

Feeling the heat of embarrassment on my cheeks, I nervously smile and shy away behind Kevin. I’d been doing that most of my life! Being so tall compared to me, it’s easy to hide behind him.

“Gary…..,” Kevin grumbles, grabbing my collar and wrenching me out from behind him. “We’ve talked about this. Guys aren’t going to find you attractive -- if every time you want to speak to them….you’re hiding behind me!”

Being yanked out, I stumble.

“Kevin!” I whine, brushing myself down as he lets go. “Why you gotta be like this!?”

“Just trying to look out for my brother from another mother,” he answers, giving me a silly smirk. “Just go ask him already!”

Grabbing my narrow shoulders, Kevin then turns me on the spot and pushes me in Ash’s direction. Stumbling again as my feet catch up with my legs, I turn back and give him a worried look.

I feel my heart thumping away and I instantly start rubbing my hands again, for comfort.

“Go on!” Kevin then calls out, pointing in Ashley’s direction.

I turn and see him sitting alone at the edge of the school field.

Still anxiously rubbing my hands, I set off in his direction. At least he’s alone!

As I get closer and closer, my nerves get worse. I feel myself trembling at the prospect of being turned down. I wasn’t even sure if he is like me. I’m just going on how….feminine he appears to be sometimes. Kinda like me

The urge to turn around and run away was building and building. Just as I consider quitting my endeavor, he turns around and spots me.

His face lights up and a big smile reaches from ear to ear.

That’s a good sign….I’m sure!

“Hiya Gary,” Ash happily greets me, patting the ground next to him for me to sit.

“H-hey,” I reply, slowly sitting next to him.

“You ok…?” he asks, flicking his boy band long hair from his eyes.

“Y-yeah,” I mutter, looking down at my feet.

“Are those boys giving you grief again…!?” Ash then asks with a concerned tone. “Why do people have to be so mean!”

I briefly look up at his worried expression and shake my head from side to side.

“N-no….,” I mumble, swiftly looking back down at my feet “They’ve been leaving me alone more recently.”

“Good!” Ash quickly replies, gently touching me on the knee. “You should know how brave I think you are. You’re an inspiration to me y’know.”

His expression would suggest he’s not joking!

“Y-you…are…?” I ask, feeling encouraged by this turn of events.

“Oh yeah!” he replies, continuing to smile directly at me. “More than you would know!”

With him smiling at me with his big beautiful blue eyes, I couldn’t help but feel even more attracted to him. He’s so pretty for a boy!

Still holding his hand on my knee, Instinct was taking over. I knew this was the best chance I’d have to ask him to the prom.

“H-hey…Ash,” I say, feeling a surge of adrenaline through my veins. “GO TO PROM with me!? I blurt out.

I watch as my words make his expression change and his cheeks glow bright red. In that second, my heart sinks.

“Are you serious Gary…?” Ash queries, fumbling and folding his arms tight. “I’m all for solidarity, but I thought you knew…!?”

I can’t bring myself to look at the confusion on his face any longer. I quickly return to staring at my feet and rubbing my hands.

“I’m sorry Gary,” he says, sighing. “I thought you’d got past this. You know I’m not your type! Please don’t give in to those boys and the peer pressure to be normal.”

Rubbing my face, I feel my body deflating from the rejection.

“Y-y-you…into girls…?” I mumble, itching my hand.

“I thought you knew that about me!?” Ash immediately asks as I consider running as fast as my little legs can take me.

Quickly standing to my feet, I throw her a quick look and a wry smile.

“I should go!” I cry, rapidly running back towards the school.

As I run off and my feet thud against the grass, I hear Ashley calling out to me. Even if I wanted to, I couldn’t bring myself to face him. I just wanted to have the ground swallow me up!

As I get closer to the school and Kevin, I see him looking worried.

Knowing he’d have questions, I didn’t want to talk about it. So I run for the nearest door.

“Gary!?” he shouts as I run past him. “What's going on!?”

As I swing open the school building door, I turn and see Kevin chasing after me.

“Leave me alone Kevin!” I scream, slamming the door closed behind me.

Like the good friend he is, Kevin does chase after me. He finds me hiding in an empty classroom. After a good few minutes, the sting of rejection eases enough for me to tell him what happened.

Much to my surprise, Kev actually had an idea of how to help me. Desperate and so very curious as to what it is, I’ve agreed to go over to his house later that evening.

Still feeling pretty crappy from my rejection earlier, I have high hopes that his idea isn't going to be one of his crackpot schemes like normal.

Knocking on the door, Bella answers and greets me with a warm smile. She’s Kevin’s slightly younger sister. She is actually really cool and has been such an ally to me!

“Hey, Gary,” she says, moving aside and letting me step in.

Stepping past her, I give her a friendly nod.

“Is Kevin about..?” I ask, removing my shoes as she shuts the front door.

Bella nods. “Yup…he is. But he’s waiting for us in my room.”

As I raise my eyebrows in suspicion, Bella takes hold of my hand and leads me upstairs to her room. Pushing to door open, Kevin greets me and holds out his hand for a high five.

“Dude,” he says, grinning.

“Hey…,” I reply, raising my hand to accept his usual stinger of a high five.

As his palm stings mine, Bella walks in behind me and perches herself on the bed. With them both staring at me, I start rubbing my hands together.

“So….. what's this about…?” I question, noticing how Bella’s gawking at me.

That’s when her staring turns into a beaming wide grin.

“You like this boy Gary!?” she quizzes, jumping up from the bed with zest.

“Who….Ash?” I ask in reply, turning to look at Kevin with wide eyes.

“Yes!” Bella squeals, turning away and opening up her closet. “How far would you go to be with him?”

Still looking at Kevin, he gently smiles and nods for me to answer the question.

“I dunno….,” I mumble, still rubbing my hands together in discomfort at the situation. “I guess I do really wanna go with him.”

“Great!” Bella giggles.

As Kevin looks in Bella’s direction, my attention is drawn to her. Holding up a pleated white skirt, she winks at me as we make eye contact.

“We wanna make you the girl of his dreams!” she cheers, wafting the skirt in my direction.

“You want me to dress as a girl…?” I grumble in concerm, turning to give Kevin a rather unimpressed look.

That’s when Bella steams over and holds the pleated skirt up against me. I look down and I see just how excited Bella is at the prospect. Do they really think this is going to work?

“I dunno…,” I mutter, now feverishly rubbing my hands together.

“Don’t look so worried Gary!” Kevin chuckles, confidently patting me on the arm. “You’re already a little effeminate, so it should be easy!”

“What about—” I groan then I get cut off.

“Stop worrying!” he laughs, patting me again on the side. “I’ve got it all worked out!”

Now frowning with worry, my mind wonders what the other kids at school may say. I’ve already come out as gay, now I’m going to have to crossdress!

“Here’s my plan!” Kev declares confidently, putting his hands on his hips—like a wanna-be superhero. “I’ve already cleared it for you to stay here for the next three nights of school. That way you don’t have to see your parents dressed as a girl.”

“Right…,” I flippantly reply, watching Bella move back to her closet.

“Bella here is going to clean you up and show you the ropes,” Kevin continues, giving me a wide grin. “You’re both about the same size--so we reckon you will fit into her stuff!”

That’s when Bella turns and holds up a long blonde wig. She gives me a cheeky smile.

“Shouldn’t be too hard to make you look incredibly pretty!” Bella giggles. “A bit of shaving here and a pluck there-- and you’ll be a pretty princess in no time!”

A princess? I consider that for a moment.

“Are you sure about this?” I nervously ask, feeling like I’d just be getting in everyone's way. “I mean, Bella—are you sure you wanna let me wear your clothes?”

“I’m ok with it!” she quickly answers, placing the golden blonde wig onto the bed. “I’m actually pretty curious as to what you’re going to look like. Plus, will be nice to kinda have a sister for once.”

“So it’s settled then!” Kevin cheers.

Looking at Kevin’s cheerful face and Bella pulling out endless reams of clothing, I didn’t want to disappoint either of them. I guess it’s worth a try!

“So how's this going to work?”

Throwing me a glance, Bella waves her hand in my direction.

“Well first off, let's get you out of those clothes.” She commands. “Then straight into the bathroom for a deep bath and a close shave.”

For the next few hours, Bella is all over me! I shaved my legs and armpits. She shapes my eyebrows and paints my nails. Then after some lotions and potions, she handed me a pair of her briefs.

Thankfully it wasn’t anything to lacey! It was just a pair of plain white feminine panties. She then matched that with a thick-looking padded white bra. She did have to help me put that on.

Then came fitting the wig. I wasn’t too keen on the idea of pinning it to my hair, but once she was finished, it actually felt really natural to me.

I loved how I could flick it about as I move and how much more feminine it instantly made me appear.

The rest of that night was an eye-opener. Bella spent hours teaching me things about girls. How to walk. How to handle my hair. How to flaunt my legs and figure to excite the boys. We even practiced my voice. She had me truly feeling confident about myself. So refreshing!

The next morning went by in a flash. Bella had me up early to do my hair and makeup. I tried my best to follow her steps and learn what I could, but my tired brain wasn’t allowing it.

It wasn’t until she handed me my clothes for the day….did I perk up. It wasn’t long until I was wearing knee-high socks, matched with a tight black short skirt and a cute little top. If Bella wanted to make me look preppy, she certainly succeeded!

It’s a truly surreal experience to see a girl staring back at me in the mirror. I didn’t recognize myself at all. I think from Kevin’s reactions to my transformation, he was a little taken back too. I’m pretty sure I caught him checking me out at one point.

Let's just hope his girlfriend doesn’t catch on to who I am. She’d probably start getting all worried again!

“Are you ready for this Grace?” Bella asks me, brushing my long hair straight.

Grace is the name that we’d given my female persona. I like the name, so I didn’t complain.

“I think so!” I answer, giving her a warm smile. “I already know it’s going to be easier today to be more myself. No judgment from anyone for being a little more feminine than the other boys!”

Bella giggles and nods her head.

“Thought you’d like that,” she replies. “Hopefully this Ash boy will find you attractive too!”

We weren’t just leaving this to chance, Kevin had come up with a five-step program to get Ash to fall for me. Essentially, for the first two days at school as Grace, we’d sow the seeds.

Introducing myself to him as Grace, with the classic clumsy school hall collision, was first.  Then once we are talking. I’d use what I already know about him to make it seem we are a match and so on and so on.

Those first few days went by so quickly. I wasn’t expecting to enjoy being treated like a girl so much! Even the conversations with Ashley went down without a hitch. Must have had something to do with my super sexy feminine charms!

I’d really nailed the sexy hair flip and the cute baby doll eyes!

That brings me to the last day at school pretending to be Grace. We couldn’t keep this up for too long otherwise teachers would start asking questions! That meant that I had to ask him today at the break.

Pulling back my long blonde hair as it gently flutters in the wind, I spy Ashley walking across the field alone, as he often does.

“Are you going to ask him then?” Kev whispers in my ear as he gently pushes forward.

Tucking hair behind one ear, I turn to Kevin and give him a confident grin.

“That boy is mine,” gleefully cheer, pulling up my skirt to reveal a little more leg.

“Bella’s got a cute little prom dress already picked out for you!” Kevin chuckles in reply, egging me on.

He’s not lying, Bella’s already shown me the pictures and the outrageously high heels that go with it.

This time I strut over to Ash with confidence. Swaying my hips and strutting my stuff, I’m soon standing just behind him.

I playfully cough to gain his attention.

“Hiya Grace,” he says, greeting me with big wide eyes and a beaming smile. “I like your cute skirt.”

Blushing a little, I flick my hair all sexy—as I’d practiced.

“Thanks!” I reply, fluttering my eyes.

He was also looking particularly cute today. With His tight ripped skinny jeans hugging his skinny little figure. Along with that sexy boy band hairdo, just slightly covering his eyes and face.

“I like what you’re wearing too,” I continue, pointing at his cute, almost feminine-looking leather jacket.

Ash looks down at himself then quickly looks back up and me and grins.

“Yeah?” he asks. Looking a little smug “You’re always welcome to borrow it if you like.”

A boy is offering me his jacket to wear! That’s so goddam cute!

“Thank you,” I quickly reply, bashfully looking away and turning red.

Then, refocusing my mind on the task at hand, I look at him with a steely determination. I stand tall, puff out my chest, and pose like a supermodel.

“Ash,” I confidently blurt out, looking directly at his big blue eyes. “Do you wanna go to prom with me?”

As those words linger in the air, I stare at Ashley’s vacant expression. He’s not given anything away and the silence is killing me!

Then, slowly, his eyes grow larger and his smile wider and wider. He looks happy!

“Oh My God Yes!” he yells, throwing his arms up into the arm and wrapping them around me tight. “I didn’t think you’d be into someone like me at all!”

As he hugs me tight, I feel myself getting excited. Pulling away from his grasp, I pull my skirt down to hide said excitement.

“Oh excellent,” I say bashfully, hiding my true gender from him.

“It IS……excellent!” he then cheers, clapping his hand and gently brushing hair from his face. “I’ve got a killer dress for the prom! I can’t wait to wear it.”

Wait!? Did he just say dress!?

Does he know I’m crossdressing? Is he taking the Micky out of me?

“What do you mean…….,” I pause and awkwardly smile. “A dress?”

Ash rolls his eyes and taps me gently on the shoulder.

“I may dress like a tomboy at school Grace,” Ash sighs, giving me an odd look. “But I do like to sometimes get all made up and look pretty y’know.”

A little taken back, I stutter and start rubbing my hands together.

“Y-you like to d-dress as a g-girl?” I question, now franticly rubbing my hands in genuine confusion.

Ash huffs and goes a little red. Then he looks down at his feet.

“That’s not nice,” he mumbles, almost sounding like I’ve upset him. “Just because I’m not the girliest of girls – like you, that doesn’t mean I don’t like wearing a dress on occasion!”

I gawk at him staring down at his feet. Things he’s said and done flash through my mind. Things that made me thought he was gay at first, but now they are starting to add up to something else.

I think…..Ash might be a—girl!

“You’re a girl!” I exclaim, with all the grace and politeness of a bull in a china shop.

He slowly looks up and I see the daggers forming in his eyes.

“Yes!” he sharply answers with a growl. “I’m a girl! I thought you knew that.”

I step back in shock. All this time! I never knew! How did I not see!?

“Holly biscuits!” I yelp. “We’ve been friends for all this time and I never knew!”

That’s when her face stops being angry but confused.

“Sorry?” she grumbles, looking me directly in the eye. “We’ve only known each other for a few days?”

Stunned at how quickly she’s cottoned onto my charade, I step back and quickly look down at the floor. I could hardly hold back my anxiety at this point. Rubbing my hands together almost felt like I’d worn them down to the bone.

“Wait!?” she squeals, pointing at my nervous habit.

I shy away and my instant reaction is the bolt for it. I wanted to run to my safe hiding place and hope that Kevin doesn’t find me this time!

“G-gary….?” She asks softly, leaning towards me, trying to look through the hair now covering my face. “Is that you under all that makeup Gary?”

I don’t want Ash to hate me, so I confess. I nod slowly, but I daren’t look her in the eyes.

“Oh Jesus Gary,” she whines, exhaling and slapping her forehead with her hand. “I can’t believe you didn’t realize I’m female!”

“I j-just assumed,” I timidly reply. “I g-guess it’s that you’ve got shortish hair for a girl,” I continue, trying to explain myself.

Still too nervous to look her in the face, I hear her loudly exhale. Then weirdly……it sounds like she clicks her fingers several times.

Instantly, I start to feel weird. The hair covering my face quickly recedes and with my face uncovered, I see her staring at me with a smug grin.

Then, like a balloon popping, I feel my crotch snap back inside me. I squeal!

“Funny,” she giggles. “Seem’s people might mistake you for a boy with that pixie cut you’re sporting!”

My mouth falls open and I look up at her in fear.

What the hell just happened? Why does my chest feel heavy and why does my crotch feel so empty!?

“I’m happy to go with you now….Grace,” Ashley laughs, putting emphasis on my fake female name. “Now that you’re a real girl of course!”