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Chapter 4
by SomeoneYouKnow
What did you pick?
Pick the skimpy schoolgirl outift.
Oh God, you can't believe you're actually going to do this. You might as well go all out, but still... this is just too much. Yet you can't help but look at it.
It's slutty and very outlandish. Something someone would dare someone else to wear out in public.
The top shirt is a schoolgirl outfit, like something from a porn parody of a high school girl. The shirt is way too small, making it a crop top. It's open down the middle, revealing your chest.
There's a bow tie too, but it just ties around your neck. The mini skirt is crazy enough, but it's even shorter than the goth outfit skirt. It's paired with thigh-high socks.
Oddly enough, you want to wear this, even though your body tells you no. It's just simply too much. But you can't help but be drawn to it. Why the schoolgirl outfit? The sundress is modest, and the goth girl is... eh. But this...
"You okay, Ash? You keep staring at the schoolgirl outfit," your sister Rachel says, snapping you out of your trance. You sigh. You can't believe you're actually doing this... Your hand touches the schoolgirl outfit.
Her eyes widen, and she can't believe you picked it. "Holy shit, I can't believe you actually chose this," she says, taking the other two outfits off the bed. "I'll leave you to it then. Uh, yeah, that's about it, I guess..." she says as she leaves your room, still in shock.
Looking at the goth outfit, it's a skimpy top, a mini skirt, and thigh-high socks. You can't believe you picked this option at all.
The weird part is that your heart is beating fast. You put your hand over your chest and feel your heart thumping. You hate this, every single second of it. You know you're going to school, and your friends are going to laugh at you.
The boys will look at you with hunger, wanting to get a piece of your yummy ass. Treating you like the slut you are.
You shake your head, trying to get those thoughts out. You don't know where they came from, but they just happened. You don't know what's going on with you at all.
And yet, what is this feeling? Excitement? Arousal...? You don't know, and you don't want to know. Gulping down your fear, you lift the outfit off the ground. Then you see something drop on the ground. It's your sister's underwear... A see-through bra and a thong.
Scrunching your nose, you lift it up off the ground with one finger. Ew, just ew. You set it on the bed and roll your eyes. Your sister probably left it in there by accident.
Looking at it out of curiosity, you reach out to feel it. You've never once touched a girl's underwear before. It feels different. A lot smoother and softer compared to the briefs you're wearing.
You wonder what it's like to wear it...
You shake your head, trying to get that thought out of your head. This is wrong and disgusting. This is your sister's underwear, for God's sake.
You shouldn't be thinking this way. You're a guy, you don't need feminine things. You shouldn't even consider it.
But... you kind of want to wear it...
Hearing your own thoughts a second time, you bite your lip as your heart quickens. It would probably shape well around your ass. The bra itself would be a new experience.
Do you dare?
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Catching New Feelings
Highschool Crossdressing Extravaganza
Taking an opportunity to crossdress, you discover new feelings about yourself that you never felt before. But you’re not the only one who is discovering new feelings. With your new appearance, your friends start having a new perspective and feelings about who you are as a person.
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- Feminization, Crossdressing, Sissy, Gay, Highschool, Romance, Nerds, Jock, Bully, Dare, Submission, Submissive, Confident, Unwilling, goth girl, Goth
Updated on Dec 13, 2023
by SomeoneYouKnow
Created on Apr 20, 2021
by SomeoneYouKnow
With every decision at the end of a chapter your score changes. Here are your current variables.
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