Jack's Story (Top Tier Reward Story)

Thank you YellowNinja for your support :)

I hope you like what I was able to come up with!

Here is Jack's story. A very hidden crossdresser in the Sonya's Story universe! I hope you like it. (Jack's story could be continued if you guys like it)

Jack’s Story

Early summer does make it a little easier when it comes to lunchtime. Not having to stuff the entire school into one tiny cafeteria building does make it easier to find an empty seat away from the other kids.

As I exit outside to the warm summer breeze, with my food tray in hand, I’m able to spot easily a place for me and Andrew to sit away from the annoying popular kids.

“Wanna swap your strawberry milk for my chocolate?” Andrew asks casually, ambling up behind me without a care in the world.

As we walk towards my chosen safe haven, I turn back to look at him with a sour expression.

“No dude,” I reply, shaking my head. “If you wanted strawberry…why didn’t you get strawberry.”

“Ah man….,” he grumbles with a despondent frown. “I got distracted!”

That’s not usually for him if I’m honest. If I didn’t know him better, I’d say he’s whacked out on the scooby snacks. I think it’s that generally vacant look in his eyes.

Sitting on the shaded bench that overlooks most of the school courtyard, Andrew throws himself down next to me without caution. He almost chucks his entire lunch down his front.

“Whoa,” I hiss, pushing at his shoulder. “Be careful will you!”

Andrew doesn’t reply, he just pulls a dopey grin and stares forward like he’s in a complete haze.

“So….,” I say In curiosity, unwrapping my food. “What distracted you enough for you to pick up the wrong milk?”

Andrew mumbles something for a second then picks up his chocolate milk and glares at it.

“I’m gutted—Y’know…,” he huffs, swiping his messy and matted hair from his eyes. “I saw her and she was alone. I think I just missed my chance to talk to her”

I think I know what he’s talking about. It's all he ever talks about.

“Lara Maxell..?” I pose with a mouthful of food. “Not this again man….I tell you—she ain't interested in guys like us.”

Slurping at his chocolate milk, Andrew turns to look at me with half-open eyes. Why did I become best friends with such an odd guy?

“I thought you hated chocolate?” I mock, holding up my strawberry carton with a smug grin.

“I do,” he answers between sips. “Truth be told, amigo—I saw Lara getting some…so I wanted to get some too.”

Exhausted by his almost stalker-like behavior, I rub at my face.

“She was alone then…..?” I query, leaning against the cold brick wall behind the bench. “Maybe you did miss your chance. She’s never without a whole crew of plastics following her around.”

“Nah dude,” Andrew replies with unusual energy and wide-open eyes. “I’ve heard she’s not popular anymore or something….”

“You have?”

“Yeah dude….,” Andrew continues, scratching at his matted hair. “Get this—so I heard she broke up that jock Barry. S-she’s completely free….. for me to swoop in!”

“C-come on man,” I reply with angst in my voice. “Don’t mess with Barry. You r-remember what they were like to me.”

Andrew’s face lightens up and he gives me a smirk.

“Yeah dude…,” he answers, gently pushing at my shoulder with his. “He’s a jerk. Don’t you think I know that?”

“Yeah…,” I sullenly reply, thinking about the deep scars they’ve left.

“You're not listening to me though Jacky boy.” He passionately continues, nudging me again. “Lara’s single! It’s now or never…right!?”

“Please don’t…..,” I sigh, allowing my shoulders to sag. “I really don’t Barry to focus on us again. I really don’t think I’d be much help if they start harassing you because of it.”

“They won't dude!” Andrew slowly chuckles, like an idiot. “I’m too smart for that.”

“I dunno….,” I reply in an instant, rolling my eyes at his misguided assumption. “They picked on me for years for that little accident after gym class.”

Andrew nudges me once more with more gusto, before looking at me with a wide smug expression. I’ve told him not to talk about it ever!

“Dude…..,” he says playfully, giving me a friendly smile. “You wore your mother's panties to school. That wasn’t a little accident.”

“Don’t remind me…,” I timidly grumble, going bright red as I relive the painful moment they caught me. “It was AN ACCIDENT.”

I knew he wouldn’t remember how I hate talking about it! I’ve only just started to lose the nickname they gave me.

“I know man….,” he replies softly, almost trying to make light of the situation. “I know. It’s so easy to mistake your mom's underwear for your own. We’ve all been there…..man.”

Little does he know I’d actually spent days choosing that particular pair of panties. Also, he didn’t know the hours I put in waiting for a chance to sneak them from my mother's room and stash them for wearing at a later date.

I can’t help myself. Her clothes just call to me. I can’t describe why. They just feel more like me…more exciting. I hate that my mom is the only girl in the house. I want to wear cute stuff, but she doesn’t own anything cute—except some of her underwear that is.

As much as deep down I know I’m completely messed up for wanting to wear my mom's underwear, I’m very glad I was able to hide this deep dark secret. Most people believed my lie that I wore them by accident.

Still, being called ‘girl pants’ for like three months wasn’t fun.

“We’ve all done it…?” I quickly question him, knowing that’s not true.

“Well…..,” Andrew mumbles, scratching at his wispy goatee. “I guess I haven’t—no.”

I narrow my eyes and glare at him for a second. Is he trying to upset me or is that his way of comforting me?

“Look,” I huff, looking down at the floor. “Just don’t go and upset Barry and his group. I don’t want to be called Girl Pants all my life.”

Andrew snorts and playfully kicks my foot to gain my attention.

I quickly look up and glare at him for kicking me. “….WHY?” I complain.

Andrew points out in front of us. Across the concrete and grass, is Barry and his troop of turds. It makes a shiver run down my spine even looking at the guy. I don’t wanna say I hate him…but I hate him.

I mean, some of them even have skateboards! What year do they think this is—Two thousand and five!?

“See dude,” Andrew then declares, as we watch his group loitering. “They won’t bother us because I know for a fact they are planning to beat up this kid in our grade called Matt.

“Who..?” I ask, having absolutely no idea who that is.

“Him..,” Andrew replies instantly, pointing at a brown-haired guy walking towards them. “That guy.”

Watching on as this Matt guy and his smaller friend approach them, I almost get PTSD. I know exactly what he’s walking into. Barry used to wait outside the school gates for me like it.

“If only I was bigger!” I growl, gritting my teeth tight as I watch Barry and his turds confront the guy.

“Dude….?” Andrew slowly probes, clearly spaced out by my reaction.

“I just wish I wasn’t so…so….small,” I grunt with pure frustration at my skinny body, forming fists with my hand. “I’d go over and help that guy!”

“Word….?” Andrew asks, again sounding like he’s high as a kite.

I feel tears and emotions welling up in my eyes as I watch them surround Matt. I can’t watch it. It’s too painful!

Angerly slamming my food tray down onto the bench beside me, I swiftly get up and storm off towards the school building.

Still forming first with my hands, I didn’t want to look over, but I could hear them arguing. I hate it! Why does Barry have to be such a dick? I have no idea why he’s even popular!

“Hey…..Jacky!” Andrew calls out, running behind me like the clumsy fool he is. “……Wait up!”

I don’t stop to look back—I just keep powering towards the building. I didn’t even want to acknowledge the strange looks I’m getting from the others around us.

“Dude…,” Andrew says, catching up as I continue to stomp. “You left your milk!”

Andrew then proceeds to shove my half-drunk strawberry milk in my face. He’s really not helping!

“You have it!” I hiss, pushing his hand from my face as I continue to walk as quick as my little legs would take me.”

“I can….?” I hear him happily ask with increasing distance.

As I approach the school building I don’t waste any time getting inside. Andrew is now clearly not following me. He’s probably not able to walk and drink my milk at the same time.

Now almost running down the empty school corridor, I push open an empty classroom door. Searching out a good hiding place, I put my back against the wall and slide down to my ass.

Letting out a long breath, I rub my moist eyes and try to shake out the memories of being bullied.

Knowing I’m now completely alone, I feel dirty about my decisions this morning. Why am I like this!?

Reaching down to my pants, I gently lift the waistline to see my mother's pink panties that I’ve stolen. I see my body stuffed into the soft material…hiding beneath my drab male pants.

I Girt my teeth.

I want to rip them from my body and throw them away!

I’m so confused as to why I even put them on! Why can’t I just walk past the washing basket without getting excited?

I lower my face into my hands.

“Sort it out Jack,” I grumble through my fingers. “Normal kids don’t steal and wear their mother's underwear!”

That’s when I hear some shuffling in the room. It strikes fear deep into my heart. Snapping my head up to look around, I see a blonde girl standing over me.

I feel the blood draining from my face as she stares down at me. How long has she been in here!? I sware the room was empty when I came in!”

“Are you……,” She utters slowly, clearly confused. “….ok?”

Terrified she saw me just now talking about wearing my mother's panties, I can’t bring myself to answer. My entire thought process was dedicated to making up an excuse to explain it.

“Do you need me to get a teacher…?” she queries, now clearly concerned for me. “You don’t look so good.”

Saving me from answering her, the classroom door almost smashes open. The loud bang of the shaking door causes both of us to jump. Likely for me, the girl sharply looks away.

“Jade!” a scared female voice screams, but I’m unable to see them. “Your brother’s in a fight! Come quick!”

Without paying me another thought, the blonde girl rushes to the classroom door. Just like that, she’s gone and the classroom door slowly closes behind her.

Allowing my heart to beat like crazy In my chest, I fold my arms tight and try to focus on my breathing.

God, I hope she didn’t hear me!?

People finding out I like wearing female clothes will completely destroy me. No one would talk to me ever again!