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Chapter 4
by SomeoneYouKnow
What did you pick?
Pick the sundress.
Looking at the sundress, it has a polka dot pattern. Feeling the dress it was soft and smooth. It looked feminine, something a girl will wear.
But you’re not a girl.
"Why hesitate? You already got a wig and make-up on. Why not go a little bit further?" your sister says noticing your hesitation.
It does look cute... But this is wrong you’re a guy, guys don't wear girly clothes. Then again your sister does have a point. you’re already past the point of no return.
"Ugh get out of my room I'll wear the damn dress," you say begrudgingly. She lightens up with a smile, "Trust me you won't regret this decision," she says excitedly while exiting your room.
You gulp, are you really going through with this? You grab the dress one last time and lift it off the bed to look at it. It was pretty... you kind of like it.
Probably looks good on a girl compared to you... but still, you can admit that it's cute. Without knowing you feel something drop on the ground while you lift up the dress.
You put the dress aside and bent down to pick up the object. It was your sister's underwear... It was a plain white bra with white panties.
Scrunching your nose you lift it up off the ground with one finger. Ew just ew. You set it on your bed and you roll your eyes. Your sister probably left it in there by accident.
Looking at it out of curiosity, you reach out to feel it. Never once, have you touched a girl's underwear before it felt different. A lot smoother and softer, compared to the briefs that 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 sake.
You shouldn't be thinking this way. You’re a guy you don't need feminine things. You shouldn't even consider it.
You kind of want to wear it...
You hear your own thoughts a second time. You bite your lips as your heart quickens. It probably will 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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