Chapter 4
by SomeoneYouKnow
What did you pick?
Pick the sundress.
You snatch the sundress and unfold it, admiring its cuteness. "So, what do you think?" your sister asks, waiting for your response.
"It's cute... But I can't wear it," you reply with a straight face.
"Why?!" she exclaims, genuinely shocked.
You burst into laughter. "Because you're in my room! Now get out unless you want to catch a glimpse of my ding dong," you say, playfully shoving her out of the room. As she stomps away, clearly mad at your joke, you can't help but chuckle to yourself.
Examining the dress more closely, you notice the polka dot pattern adorning its knee-length skirt. It's a charming sundress.
Amidst your laughter, your sister Rachel hears you and shouts from the hallway, "What's so funny? Did you steal that from a church girl?"
You retort, "Just wear it, you smart ass!" When you lift the dress to get a full view, you hear something drop on the ground. Placing the dress back on the bed, you spot it.
Your sister's underwear lies on the ground—a black, lacy piece, including her panties. The best way to describe them would be...
They're sexy underwear you'd wear for a one-night stand. You knew your sister had a kinky side, but you didn't expect this.
You pick it up and feel the fabric, finding it completely different from your own briefs. It's much softer and silkier compared to your nylon underwear.
Damn it, why do girls have it so good compared to guys?
You can't deny the temptation to wear it. It probably feels comfortable... But, of course, it's your sister's, so you shouldn't. Although, it's not your fault she left it here, especially among the clothes she wants you to wear. Hell, it wouldn't be surprising if she actually wanted you to wear it.
Besides, looking at it now, you'd probably rock the look. Feeling all sexy in black. Then again, it's not like anyone would see it... It's not like you're going to sleep with someone. Biting your lip, you make a decision...
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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