Tangerine Academy is a rather lax academy, with lots of freedom in regards to what you wear and what you do. They even let boys and girls share dorm rooms. Despite being a guy, I share my dorm room with a girl named April. She’s a really attractive woman, with dark skin, black curly hair, and an amazing sense of fashion. Meanwhile, I’m a super shy, nerdy loser, and I’m not exactly much in the looks department. I have fairly tan skin, long straight black hair, and a feminine face and body. Barely an ounce of muscle or fat to be spoken of.

April is a very free spirit. She’s often out late into the night, or even overnight. I don’t question what she does, but I can just about guess: partying or sleeping with someone. Maybe both. Thankfully, it gives me plenty of free time to indulge in my favorite hobby: crossdressing. Even though we share a dorm room, we have our own little private quarters with a bed, a desk, a dresser, and not much room for anything else, so when she gets home, I’m able to change back into my normal boring clothes without her knowing, and without panicking that she might see me crossdressed. Even if I don’t notice her come in, it isn’t like she’ll come into my room for any reason, so even if I sleep in while crossdressed, she won’t ever know.

Well, today was just another day of crossdressing while April was out, when suddenly, she came back. No biggie. I changed back into my normal clothes, but paused as I went to tuck my bra in my hiding place, an area beneath the dresser that can be accessed either from the back or by pulling out the bottom drawer (this way, if anyone happens to come into my room and snoop around, they’ll never find my clothes) as I thought I heard a weird sound. Listening closer, I heard the sound once more.

“Meow!”

A cat?

I finished changing back into my normal clothes, then stepped out of the room to see what was up. There, April was baby talking a small orange kitten, and laying out a food and water bowl for it. April heard the door open, and looked up to see me step out.

“Mornin’,” she nodded at me.

I checked the clock. 8:00 P.M., certainly not morning yet, though I suppose that isn’t really the issue here.

“Where’d you get this cat?” I asked.

“Hm? Oh, Madam Gloria? My girlfriend’s dealer found her in an alley. Neither of them could keep it, so I decided to bring her home with me!”

“Okay. I’ll ignore the girlfriend and dealer bit for now, but do you realize that orange cats are male*?”

“Hm?”

“Well, something like 80% are. So she is probably a he.”

“Oh. Okay, well, Sir Gloria, then.”

“And you’re just gonna… bring it here without asking if I’m allergic or anything?”

“Oh. Are you?”

“No, but-”

“Then it’s fine! Don’t worry, I used to have a cat back in high school! I know how to take care of them, alright? You won’t ever have to see her– er, him. Probably.”

I shrug and shake my head. “You’re lucky that both me and the school are so lax. I don’t mind cats, but aren’t you out often? It might get lonely.”

“But aren’t you always here?”

“Well, sure, but-”

“Then there’s no problem! You like cats, right?”

“In theory?”

“And don’t worry! I’ll be sure to clean the litter box, and make sure she has scratching posts so she doesn’t mess up the furniture or anything, and I’ll make sure she has food and water every day. You don’t even have to play with her if you don’t want to.”

“I don’t think this is a good idea, but I won’t stop you.”

“Don’t worry! I’ll bring my girlfriend over here sometimes instead of always going over to her place! I like going over there because we don’t have to worry about noise there. We’ll try to be quiet, though, I promise!”

“Please…”

I won’t lie, the thought of two attractive college women having sex in the room next door is kinda hot. But I digress.

I leave April to go about her business of setting up stuff for the cat. A while later, a friend of hers comes over with some cat litter, a litter box, a scratching post, toys, and some other stuff. She plays with and coos over the cat for a bit before going into April’s room with her. I don’t hear any noise, and drift off to sleep rather quickly.

In the morning, I hear someone knock on my open door, and call my name.

“Max?”

I mutter, and sit up in bed, staring groggily at the woman at my door. April is holding a lacy black bra, looking confused.

“Hey? Did you have a girl over last night or something? Sir Gloria was playing with this bra when I found her– him– in the morning. It isn’t mine, and it isn’t my girlfriend’s either.”

A wave of panic rushes over me.

“Uh– yeah! I– yeah. She, uh, left before you got here. She was in a bit of a hurry.”

“Is that so?” her eyes seem to glance over to a corner of my room. I follow her gaze.

Leading out from the back of my dresser is a small trail of clothes. A pair of panties, a skirt, and some knee high socks have all been dragged or partially dragged away from my dresser. There’s also a thong by the door.

“She’s very forgetful,” I tell April.

“I see… And what is her name?”

“Uh. Chloe.”

“Chloe… and Max? Funny.”

I fucked up. Next time don’t name your alter ego after a video game character who dates someone with your name.

April comes over and sits down next to me on my bed. I lean away from her as she studies my face.

“You know, you do have a cute fact, and nice long hair. Plenty of girls are probably jealous of it. I bet you would look cute in girls’ clothes.

“I don’t know about that.”

She lays a hand on mine. “Come on! Don’t be so modest! You must surely think so yourself if you’re constantly dressing up!”

“I don’t know what you’re talking about.”

She rolls her eyes. “Look, you do me a favor and I do you one, alright? Just let me see you dressed up, and I’ll give you a kiss! On the lips!”

“I uh– I don’t think your girlfriend would like that.”

“She doesn’t give a shit! She’s right outside your door watching if you want to ask her yourself.”

I look at my doorway, where a cute Japanese girl is leaning in to look into the room. She’s blushing and smiling.

“Well, if she gives the okay…”

I usher the girls and cat out of the room so that I can change in peace. I choose a black skater skirt, a long sleeve red top with lace on the sleeves, black thing highs, and a pair of canvas shoes. I also stuff my bra with a pair of fake boobs that I got online. When I’m done, I step out of the room so the girls can see.

“Oh! You look amazing! Right, Candice?”

Candice nods her head. “You look really cute.” She blushes quite a bit as she speaks. “My brother also crossdresses, so I don’t judge you for it.”

“Oh, but he’s a high schooler, before you go thinking that maybe we can hook you up or something,” April says.

“I’m not interested in guys, anyhow,” I shrug. Hell, I’m so into girls that I only ever want to wear girls clothes, for a matter of fact.

“Okay, you did what I asked, so time for me to pay up,” April says, stepping up to me. I sweat a bit as she stands so close.

“Is he also wearing panties?” Candice asks, suddenly behind me. She kneels down, and lifts up my skirt, catching a glimpse of my black compression panties that are supposed to hide bulges.

I let out a shriek, but it’s stopped mid-shriek by April, who steals my lips away into a kiss. When she lets go a second later, I nearly fall backwards. I excuse myself to the couch, and sit down, overwhelmed.

The girls sit down on either side of me, and April asks if they can do my makeup. I’m not in a place where I can say no, so I just nod my head. Candice goes to April’s room, and returns with a makeup kit. I can’t recognize half of what she pulls out, and couldn’t even hope to summarize it all. Once she finished doing my makeup and nails, she brings a hand mirror so I can admire her artwork.

“Wow,” is all that I can say. It isn’t like it is a super dramatic change, and thankfully I don’t look like a drag queen with over dramatic makeup, not that there’s anything wrong with that, it just isn’t my taste. But I do look cute.

“I’ve always wondered how I would look in makeup,” I admit. But trying it on my own is impossible, due in part to the steep learning curve, as well as the fact that even if I have some privacy, I don’t have enough to be able to practice makeup. The smell of nail polish remover, for instance, would be too obvious.

“I can teach you some time!” Candice offers. She seems really excited. This must be one of her hobbies, I guess. I nod my head.

“So, have you ever considered going out like that?” April asks.

“Are you mad? I can’t have people know that I like to crossdress!”

“Why not? Not like the school would care. Plus, it’s 2023. Nobody gives a damn anymore.”

“I assure you that, yes, they most certainly do!”

She shrugs. “Well, it isn’t like anyone would even know. A bit of makeup, a different hair style – oh, shit! We gotta do your hair!”

April runs off to get some hair ties and stuff. I let her do as she pleases, with the only rule being not to cut it or otherwise permanently alter it. After she finishes, she puts a pair of fake glasses on me, and gives me the mirror once more.

I can see what she was getting at earlier. While I might get mistaken for my sister or such by someone who is familiar with me, anyone who doesn’t know me well might as well think I’m someone completely different. I feel as if I’m almost indistinguishable from a real girl.

“I have to admit, you two are good,” I say. My hair has been done up in a half ponytail, and the glasses seem to frame my face quite nicely.

“Right! So what do you say? Wanna head out?”

I groan, but nod my head. I can’t help it. I’m practically at these girls’ mercy. Moreover, I can’t help but admit that it might be a lot of fun.

First things first, I get changed into the school uniform. The school kind of doesn’t care if you wear it, or if you’re lax in wearing it. But they provide one free uniform each year, and you can buy more at the school store. While there are a few different variations, this one consists of a red skirt, white button up shirt under a red button up vest, with a red blazer over it. It is adorned with navy blue buttons and accented with navy blue lines around the cuffs and the bottom of the skirt. There’s also a navy blue ribbon.

“You look so cute in that! Personally, I hate uniforms, but seeing someone else in one is really fun!” April tells me.

“I never bother wearing mine, but wearing the girl’s uniform is much better,” I nod my head.

Today is a day off, but we’re still allowed to wander the school. Each of us brings a bag with us, though April has told me not to look into it since it’s a surprise. I don’t know where we’re heading, but I’m figuring we’ll probably have a picnic or something somewhere. Also, since it’s hot, I opt to go without the blazer.

Instead, about 10 minutes later, I find myself standing at the front gates of the gym. The gym is pretty large, and hosts a basketball court inside, as well as some outside courts and a running track. I pause, and look around.

“Surely this isn’t the place you’ve been planning to bring me?” I ask.

“Yep!” April confirms.

“But… why?”

“Well, wearing the uniform is one thing,” Candice says, “but there are other everyday aspects and outfits that you wouldn’t ever get the chance to wear, right?”

“What do you mean?”

“Why don’t we head inside and find out?”

“You don’t expect me to go into the women’s changing room, do you?”

“Were you going to enter the men’s? Come on, it’ll be fine! There’s nobody around, and we’ll be there to keep watch.”

Hesitantly, I follow her in. The gym is empty, as promised, save for a pair of guys at the basketball court. We ignore them, and head straight into the women’s changing room. There, I’m finally allowed to look into the bag.

Inside of the bag I brought with me is an athletic shirt and women’s running shorts. The shirt is white, while the shorts are red with a white stripe running down the sides. They look really short.

“I don’t know about this,” I say, looking at the women’s gym uniform.

“Let’s hurry up,” April says, throwing off her shirt. I gasp, and turn around. She just laughs at me.

“There isn’t much to see anyhow,” Candace tells me.

“Hey! Watch it!”

I ignore them, and focus on changing. I start with the shirt, as it isn’t that big a deal to be seen shirtless. But even then, my face flushes red as I feel the girls’ eyes staring into my back.

More hesitantly now, I slide my skirt off, which is met with a round of applause.

“Hey!” I scold them, turning back. I shouldn’t have done that, as I see that both girls are just standing there in their underwear. “I’m sorry!” I shriek as I turn back.

April grabs my hand, and forces me to turn back, and pulls me towards her.

“Do you think we would have done this on accident? Go ahead, enjoy the little show,” she winks.

As previously stated, April doesn’t have much going on up there, but I’m still mesmerized. Candice is slightly more stacked, and equally mesmerizing standing there in her bra and panties.

My mind goes numb and I just stand there for a bit. The girls laugh, then continue dressing. Slowly, I turn back, and grab the running shorts, changing into them quickly. After changing, I look myself in the mirror. The compression panties are doing their job, that’s for sure. Thankfully, I’ve always been tiny. As I’m admiring myself, April comes up behind me, and pinches my ass.

“Alright, Chloe! Ready to go for a run?”

“No?”

And yet I’m forced to do it anyways. I nearly die. We spend maybe 30 minutes out on the track, with the girls running laps around me. Finally, they take pity on me, and bring me back into the gym AC, and run to get me some water. As I’m sitting down, a pair of guys come up to me, the ones from earlier.

“Hey, girl! Don’t think I’ve seen you around here before. You here alone?”

“I– uh… No, my friends are coming back in a bit.”

“Oh, good. We were worried when we saw you here alone. There are lots of bad guys out there, you know? And besides, you look pretty bad – not to say, I mean– you’re pretty, you know? But you look like you’re exhausted. Can we keep you company until your friends come back?”

“Uh. I would rather not.”

“Alright. We won’t bother you, then. We’ll be nearby in case someone gives you trouble, though, alright? Just holler if you need help.”

“Okay?”

“Cool! And if you change your mind, you know where to find us.” The guy winks at me, then the pair walk off.

I have to admit, I panicked more than a little bit. Firstly, I thought they might hit on me, or even force themselves onto me. Or they might tell that I’m trans. But they seemed really nice! I almost consider getting their phone numbers, but shake the thought out of my head, just as the girls return.

“Hey, Chloe! We’re back! Here's some water and some chips!” April says, handing me said refreshments. She glances over at the guys, who nod their heads at her, and walk away. “Nobody gave you any trouble, right?”

“No. Those guys were nice.”

“Hmm? Would you rather we leave you hear with them?”

“No!”

“Good! Let’s go get changed, then, but this time, no playing around, alright?”

“Okay?”

This time, there’s less fooling around in the changing room. I then follow the girls out towards the dorm. Instead of heading in, though, we walk out to the parking lot, where Candice’s car is parked, and they tell me to get in.

“Uh… why?”

“Isn’t it more fun to get surprised? Come on!”

I pause, and look around. If I’m kidnapped, will anyone notice me? No, certainly not if I’m dressed like this. Ah, well, these two have been nice so far, so I’m sure it’ll be fine. I shrug, and enter the car.

To be continued…