Chapter 5
by SomeoneYouKnow
Do you dare?
Regain your sense.
You slap yourself to regain your senses. You shouldn't! You have gone far and beyond already by wearing a dress. This is wrong in so many ways.
You grab her underwear and toss it out into the hallway. "Hey, Rachel your underwear's in the hallway," You scream to her. "Thank you, I was looking for that." She replied back.
You bite your lips and couldn't help but imagine what it would be like to feel it, the softness, the silk... but you stop yourself from dwelling deeper.
With that out of the way now. You have to face another one. The dress... you gulp as you lift it off the bed. It was pretty but not your style.
Considering that you’re a guy it's natural to dislike wearing something like this.
But here you are dress in hand about to wear it. Taking off your clothes you slip on the dress. You breathe heavily when you finally dawn upon the dress.
It fit you oddly perfectly like it was meant for you. The feeling of the skirt hitting your hairless leg felt tingly. Like a wave of electricity hit you. It was sensitive to the touch.
You should've stopped your sister from convincing you to shave your whole body. But she kept on annoying you to the point where you had enough and you just did it.
You want to go back on that decision now. Your ass feels so ****. You can feel the air and how free it is just hanging there.
You really didn't want to look at the mirror to see your final look, it was too much for you already. But curiosity won you over.
You bite your lips and turn around to face the mirror. There stood a pretty girl staring back at you. You let out a gasp and cup your hand to your mouth. The girl in the room did the same.
This can't be... this shouldn't be. You didn't expect to look exactly like a girl. You stood there for a solid minute. Processing what you’re looking at.
You thought you would look more manly. Like a guy in a dress, it stands out. But this kind of result... you didn't know you were that feminine.
Your mind's telling you no, yet your body is telling you yes. You couldn't help but turn around to examine yourself. The wig looks natural on you like you've grown out your own hair.
You’re in disbelief at what you’re looking at. This can't be you, but it is. This is your body and that girl in the mirror, was you.
"Hey, Ash you okay in the-?" your sister stops mid-sentence as she walks in and looks at your outfit. "This isn't right," you say to her still in disbelief.
"This isn't right? Have you looked at yourself? It's like the dress was made for you," she says stepping closer and touching your skirt.
"It should be worn by a girl, not a guy," you say seriously. She then grabbed your head and made you look in the mirror.
"How can you say that when you look like that," she says frustrated at your own denial.
There you were in the mirror the pretty girl in the room. Before you can refute that fact. She grabbed your hand and lead you outside. "Come on now we can't be having a second-minute decision right now. You're going to be late for school."
What's next?
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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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