Drake and Jasmine Episode 1: The First Day

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My mother has gotten remarried, and I'm really happy for her! Her new wife seems like a wonderful woman, and her daughter seems nice, too. I've always wanted a little sister, really.

The following few weeks after the marriage was a bit of a chaotic mess. Several family members are mad about the "unholy" marriage and "alternate" life choices, and my mother and her wife Audrey decided to move to California in order to be able to just start anew. So now we're living in a small house, and I'm sharing a room with my new little sister, Jasmine.

I haven't gotten to know Jasmine much yet, with most of my time being spent helping my mother with the move.What I do know is that she's eight and about as adorable as you can imagine. She has really pale skin and golden hair. She has a lot of clothes, which takes up about 90% of our shared closet and dresser space, not to mention a fair portion of the floor which she never cleans. I've taken it upon myself to act like a good big brother, and clean up after her. After all, I do at least need enough space on the floor to make it to my bed on my side of the room.

The first thing that Jasmine does when she wakes up is go and take a shower. While she does that, I check that we've both got everything packed that we need for school. Our first day is today, and Jasmine seems excited. She's even woken up extra early today, and I hear her singing from the bathroom down the hall.

Eventually, Jasmine finishes showering and comes into the room wearing just a towel. I grab my towel and a change of clothes, and head into the bathroom to take my shower. As expected, Jasmine has left her clothes all over the ground. I pick up her pajama shorts, pink with hearts on them and very soft. Jasmine certainly loves cute things, and honestly, I do, too, so it's always nice seeing her run around in her cute clothes. I do wonder how the clothes feel, though. I mean, obviously I'm older so they might not fit well, but at 14 I'm still relatively small and skinny. They might fit.

I take my shorts off, and throw them to the ground. As I do, Jasmine walks in, and gives me a puzzled look.

"What are you doing with my shorts?" Jasmine asks, looking between me and the shorts.

"I'm moving them out of the way, because you just leave everything a mess. What are you doing in here, anyhow?"

"I need to pee. Do you mind?"

I sigh. "Why didn't you pee before you left the bathroom?"

"I forgot, then I got to our room and really needed to pee. I'm going to pee, so unless you want to watch, you should step into the shower. Of course, if you do want to watch, I won't stop you."

"No, no, I get it. Let me just step into the shower really quick. But first..."

I take Jasmine's shirt off the ground, and then hesitate as I look at her panties on the floor. I don't really think I should touch her panties with my bare hands. I use the shirt as a kind of glove and grab the panties, moving them to the side alongside my shorts. I throw my shirt on the ground as well, then step into the shower in my underwear. Once I'm in the shower with the curtain closed, Jasmine sits on the toilet, and a moment later, I hear her tinkle. Once she's done, she just sits there.

"Are you done?" I ask.

"Yep."

"I'm about to start showering."

"Okay."

"Do you want to leave?"

"No."

"Okay..."

I shrug, then remove my underwear, and throw it over the shower curtain rod. I turn on the shower, and start soaping up my body. As I do, I finally hear the door open, and Jasmine (presumably) leaves.

Several minutes later, I step out of the shower. I look around, and find that my clothes are gone, both my clean clothes that I was going to change into, as well as my dirty clothes. Even my towel is gone, so I can't just walk into my room in the towel. The only clothes left here are Jasmine's dirty clothes. And I certainly can't walk into my room wearing just that.

I hesitate for a moment. I check that the door is locked, then pick up Jasmine's underwear. I start slipping my leg into one of the holes when someone knocks on the door.

"You about done in there?" Audrey asks.

"Yeah!" I call back to my step-mother. I return the underwear to the pile of clothes, then open the door, covering myself the best that I can. Audrey looks down for a second, but quickly brings her gaze back up.

"You're free to wear whatever you want in this house, as far as I'm concerned. That includes nothing," she tells me.

"Jasmine stole my clothes while I was showering," I explain.

She seems surprised. "Oh? That's unusual for her! She's such a good girl usually! I hope she isn't feeling forgotten with all the moving and the marriage and everything!"

"Rest assured, I plan to be a supportive brother for her."

"Good, good! She's your little sister now, so be sure to cherish her!"

"I will."

I walk down the hallway naked, and step into the room. There, Jasmine is rummaging through her dressers for something. She looks up at me as I walk in, and giggles.

"Yes, yes, very funny," I tell her, sighing. "I'm not mad, but please don't do anything like that again."

"Shouldn't I be the one saying that? You were the one being perverted and gazing at the shorts of a little girl."

"It isn't like that!" I insist.

"Oh? So it wasn't because you're a pervert? Maybe you just like wearing girl's clothes, then? If so, then good news: I'm okay with you wearing my clothes. Here, these are new panties, I haven't worn them yet! You can wear them to school!"

"No. I'm not interested in things like that."

"I also have a dress here that's a bit too big for me. You can wear it if you want."

"No, Jasmine, I'm not like that."

"Fine, Drake," she sighs, and rolls her eyes. She sits on her bed and starts brushing her hair. Meanwhile, I get dressed because we've got school we've got to go to.

After eating, we say goodbye to Audrey (my mother is already at work) and start walking Jasmine to school. Jasmine's school is one way, but mine is off in the other direction. I don't mind doing a bit of walking, though. Back home we lived in a really rural area, and I had to walk thirty minutes uphill both ways in the sweltering heat.

Jasmine takes my hand as we walk. She skips, and hums, and pauses several times to look at bugs and flowers. Thankfully the time spent looking at flora and fauna is recovered with short bursts of speed as she runs down the sidewalk, dragging me behind her.

As we approach the corner before her school, Jasmine stops he, and tells me to kneel down so she can tell me something.

"What?" I ask.

"I brought this for you. You can wear this to school," she says, pulling a pair of white panties out of her backpack. There are pink frills on the leg holes, and a pink ribbon on the front.

"Jasmine! I can't take this!"

"Bye-bye!" she says, and runs off towards the school.

"Hey! Wait!" I shout, starting after her. I stuff the panties into my pocket, and chase after her.

As we approach the elementary school gates, Jasmine is quick to start making friends with some kids she saw at orientation. She waves goodbye to me, then crosses the threshold into the school.

"You're a good brother to walk your little sister to school like this," one of the teachers tells me. I look over and see a rather young woman, probably just around 20, smiling at me. She seems really cute, and that smile sends a shiver down my spine.

"Ah? Y-yeah. Our mothers just got married, so this is my first time dealing with a little sister. She's really cute, but I'm not really used to all of this."

"Aww, I'm sure you'll get used to it soon! Feel free to let me know if you ever need anything! I'm always here at the gates during the morning, and I'm plenty used to taking care of kids! I'm the oldest of six, and I've done lots of babysitting over the years! I'm also working as a kindergarten teacher starting today, so we've both got a bit of a fresh start this year."

"Right. Good luck with the kids!"

I would love to spend more time talking to the teacher, who according to her name tag is Ms.Drane, but if I don't hurry then I'll be late for school. So I wave goodbye, and start off towards the high school which is the other direction from my house.

I think about stopping by my house really quick and putting the panties away, but I feel like that will earn some questions from my step-mother, so I opt against it. Instead, I stop in an alleyway on the way to school, and stuff the panties in the bottom of my bag. I don't want them falling out of my pocket or something.

Still, the entire way to school, I can't take my mind off of the fact that I have a girl's panties in my bag. What if someone found it? I can't help but imagine me pulling out a binder, and the panties getting caught on it and falling to the ground in the middle of class. I might die if that happens!

Logically, there's only really one thing to do, right? I mean, if I wear them, then they won't fall out of my bag or my pocket. And so long as I wear my underwear over them, nobody will be able to see them even if I bend down or if I were pantsed.

I walk up to the school, a brand new building with all the newest technology, like bulletproof glass and bulletproof walls and bulletproof doors. Of course, they still tried to make it look artsy and pretty. I walk through the gates, alongside some students who look like jaded adults, and other students who look like literal children. With my frame, I'm probably the youngest looking of the bunch.

Once inside, I find a bathroom with no other students in it, and slip into the handicap stall. I put my bag on the ground, and slip my pants and underwear down, then unzip my backpack, and pull out the panties. I hold them up for a moment, looking at them. Am I really going to do this?

I can't help but feel a bit excited as I look at the panties. My heart pounds faster, and it feels as if my body forces me into the answer. Slowly, I slide the panties up my legs. They're a bit tight as I pull them up to my hips, and there's not much room up front for my bits, but they barely, just barely, fit. I twist my body around, trying to get a good look at my bottom in the panties. I hear a pair of students walking into the bathroom, though, chatting, so I hurry up and pull my underwear and pants back up. Then I flush the toilet, and walk out of the stall. I wash my hands quickly and leave the scene, as if I did something bad.

Just outside of the toilets, I see a young girl around my age, looking back and forth between the bathrooms. She has short hair, and a boyish face. She grabs the hem of her skirt, and hurries into the girl's room once she sees me. Ok. Weird. Then again, I'm a boy wearing my little sister's panties, so who am I to decide what's weird or not? Besides, she was cute.

I'm among the first students to enter the classroom. The seats are assigned, so I check the chart at the front of the room and take my place, and start talking to the other kids who are there. We'll be classmates for the semester, after all, and school mates beyond that, so I ought to try and makes friends with who I can. I'm coming here without any previous friends, so it's probably a good idea to make friends early so I don't end up halfway into the year and realize that I have no friends.

Some time later, as the class is filling up, the girl from earlier pokes her head into the room. She looks around, then hesitantly enters. A rather rude boy comes in right after her, bumping her shoulder and knocking her out of the way. She frowns, but doesn't say anything. Instead, she checks the seating chart, and finds herself sitting next to me. I look over at the chart, noting her name.

"Kelly Drane?" I ask. She nods her head. "Where have I heard... Oh! Your sister is a kindergarten teacher over at the elementary school, right?"

Her mouth makes an O shape. "Yes, how did you know?"

"I ran into her earlier while dropping my sister off."

"Hey, be careful," A guy behind me warns, dropping his hand between the two of us. "You might catch her sickness."

"What sickness?" I ask.

"Transexuality."

The girl just looks down at her feet.

The guy laughs. "She can't stand up for herself, so make sure to punch down on her as hard as you can!"

I smack the guy's arm away. "Like I care. I prefer people like her over idiots like you."

He sneers at me, but says nothing, instead turning back to talk to one of his friends.

"Thanks," Kelly mutters. "You didn't have to do that."

"Clearly you won't stand up for yourself, so somebody has to."

She just blushes and looks down at the desk.

As the students are talking, a girl walks into the room. She looks to be an elementary schooler, but is wearing a lab coat. She's carrying a step stool, which she places at the front of the room, and steps on, then claps her hands.

"Okay, students! Time for class! Please settle down!"

"That's our teacher?" a girl asks.

"That's right!" the teacher says, shooting her an evil look. "I may look small, but I've been dealing with kids like you for longer than you've been alive!"

"How old are you?" one of the boys asks.

"Ah, nope! You can't ask a woman her age! Just know that I've been to college for a degree to teach you kids, so I expect you to listen. Now, let me begin by introducing myself. I am Mrs. Carter, and I will be your science teacher. Science can be dangerous if done improperly, so please do listen to my instructions carefully."

Kelly looks over at me. Her eyes are saying it all.

I sigh. "Yes, that's my mother."

Mrs. Carter claps her hands. "Now, now! Just because you're my son doesn't mean that I'll tolerate you talking in class. Drake Carter, please do pay attention, or you'll get no dessert tonight."

That draws a few chuckles, but I just roll my eyes. My mother has fun teaching, and must be pretty effective at it to still be doing it after all this time despite being less than 5 feet tall.

Though there isn't much to do on the first day of school, I make sure to pay attention and get to know as many of my classmates as possible. Kelly sticks close to me in the classes that we share, as well as in between classes. At lunch, she sits at the same table as I do. Though the one kid was rude to her, most people seem to be treating her well.

After school, Kelly meets up with me, and we walk out the front door of the school together. She hands me a slip of paper with her number on it, then runs off. She doesn't say very much. Not now, or earlier during school. I don't know if she's just shy or what.

I walk out to the parking lot, where Audrey is waiting for me alongside Jasmine.

"Who was that?" Jasmine asks.

"A girl that I met," I tell them.

"Oh?" Jasmine tries to raise her eyebrows but fails. "You already got a girlfriend on the first day of school?"

I roll my eyes. "Please. She's just a friend. Enough about me, how was school for you, kid?"

"Fun! I made lots of friends! If your relationship with that cute girl doesn't work out, let me know and I'll hook you up with one of them!"

"Hard pass. Audrey, thanks for coming to pick me up. Mother has a club to advise, so she'll be home late."

"I know. She's a smart woman, so she's a good choice for the science club!"

"She's more than a little bit crazy about science, but I guess that's what makes her a good teacher."

"Exactly! You have to be passionate about what you love!"

Audrey is an artist, so I'm sure she's passionate about making art. Unfortunately, passion doesn't always convert into cash, which is what we really need. But she seems really happy.

"Are you wearing my panties?" Jasmine asks.

"Of course not," I tell her.

"Should I even ask what all of this is about?" Audrey asks.

I groan. "Jasmine thought it would be funny to hand me her panties when we got close to her school, then ran off. I had to hide them in my bag all day."

"Can you give me them back, then?" Jasmine asks.

"We're in a parking lot right now, surrounded by other students. Wait until we get home, and I'll give them back then," I tell her, trying to push the issue back as long as I can. After all, I am, in fact, wearing her panties.

"Hmm? I'll be waiting, then."

Audrey speaks up. "Jasmine, be sure to be nice to Drake! He really likes you, and he'll pay plenty of attention to you even without you being a trickster, okay?"

"Yes, mommy."

"Good."

With that, I've brought myself some time for now, but how long can that possibly last? Audrey drives us the relatively short distance back home, and pulls into the driveway. I beeline for my room once we're home, but Jasmine is right behind me.

"Can I have my panties back now?" she asks.

"I'm sweating after gym class, so let me change first," I tell her.

Jasmine, faster than I can react, grabs hold of the waistband of my pants, and pulls them down. As she does, she also pulls down by black boxers, revealing the white panties that she gave me earlier.

"So you are wearing my panties!"

"It's not like I could leave them in my bag! What if they fell out!"

"Liar! You just want to wear my panties!"

"It isn't like that, Jasmine!"

"Hmph!" she says, crossing her arms. "You know, if you just ask nicely I'll let you wear all the clothes that you want! Our mommies don't even need to know!"

"Jasmine-"

"Don't lie! I saw your eyes earlier when you were looking at my shorts, and you're wearing my panties right now! If you want to wear my clothes, just do it! You don't even need to tell me! I'll leave some panties that I've never worn to one side of my drawer and won't ever need to know about them."

I sigh. I mean, it's not like I don't want to wear these clothes, but it's so awkward to wear my little sister's clothes. But, then again, I don't really want to tell my mother or step mother about me wanting to wear girl's clothing.

"Do you promise to keep things a secret?" I ask.

"Yes!"

I sigh. "Fine. You're a sweet little sister, you know that?"

She nods her head enthusiastically. "Yeah! I just want to help! I'm not trying to be a bad girl!"

"You're not. You're just a bit pushy."

"Sorry..."

I shake my head. "It's fine. Some people need a push, I guess."

"So... Can I see you wearing a dress?"

"Uh..."

"I've already seen you naked and in panties, so nothing else could really be considered embarrassing, right?"

"I guess?"

Jasmine pulls a blue dress with a sunflower and yellow hearts on it down from the hanger in her closet, and hands it to me. It's a short dress with spaghetti straps. I kick my pants and boxers off (previously around my knees) and then throw my shirt onto the bed. Then I pull the dress on. As I do, the door opens.

As my vision returns to me, I see my mother standing at the door, staring bewildered at her teenage son wearing a little girl's dress.

"I guess you really are just like me."

My mother's first wife (my other mother) divorced her when she found out that her "husband" (my mother) wanted to be a woman. Moreover, my mother, currently wearing yellow overalls with colorful bugs on them, likes wearing childish clothing.

"It's not like it seems," I insist.

"Funny, I said that to Jessie back when she first found me dressed up, too. Just do what you makes you happy, okay, kids?"

"Okay!" Jasmine says.

"Didn't you have club activities?" I ask.

"Hmm? On the first day of school? Don't be silly, we've still got to recruit students. Speaking of, maybe you could join the science club? Sounds fun, right?"

"Whatever."

"And you can bring your girlfriend, too. Audrey was gushing about how that cute girl you walked out with."

"It isn't like that!"

My mother's eyes go wide. "Oh! The key words to prove that things are exactly as they seem! Fantastic!" She laughs as she walks away.

I groan and fall back on the bed. The dress rides up to show the panties I'm wearing. Jasmine sits on the bed beside me.

"You know, isn't this the best result? You get to wear what you like, and everyone is happy with it?"

I grab Jasmine and hold her tight. She seems surprised at first, but then pats my head.

"There, there. You're a good... kid, Drake."

Even if everyone is fine with things, stuff like this is anxiety inducing. I don't want to be vulnerable like this. And, besides, even if my family is okay with stuff like this, most people aren't. Even in liberal California, there are bigots. Even putting that to the side, most people aren't okay with adults wearing childish clothing like what I enjoy. I can't get together with a cute girl like Ms. Drane (the teacher not the student) or anyone else if I'm like this. Mother got lucky, but most people aren't as weird as Audrey.

"It'll be okay," Jasmine promises, hugging me tight.

I fall asleep like that, with Jasmine in my arms. I wake up in the morning confused. I look down at Jasmine, who smiles at me, and with that smile, most of my anxiety melts away. Not all of it, of course, but I'm happy to know that I can be open with Jasmine, my mother, and Audrey. At least while I'm home, I can be me. Everything else can be sorted out later.

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