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General RP When pants just don't cut it...(Liz and Knight_of_None)

Liz

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Joined
Nov 10, 2024
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48
Gerald kept glancing at the bedroom window.
He was in his sister's bedroom....to be more exact, he was rummaging through her dirty clothes basket, the same thing he'd been doing for at least 3 months now. The 18 year old had what some called slightly fem features but he never considered himself a crossdresser or a sissy. Nevertheless, there was something about the way it felt to pull up his sister's nylon panties, fitting snug on his crotch.

At first it was just her panties he put on...then he began putting on her bras. They fit tighter than her panties and more than once he was afraid he'd rip them trying to take them off....how could women wear these things? bras must've been invented by a man....

Gerald posed in front of the mirror....he had rolled up socks in the bra cups, resulting in a somewhat misshaped figure. Then he turned around and glanced at the lipstick she left on her make up table.
Aww, what the hell....it wouldn't hurt....besides, sis wouldn't be home for another 4 hours....

Gerald pursed his lips like the way he saw his sister do it a dozen times and tried....as expected, it wasn't as if he could draw within the lines.

He knew their mother had a couple wigs due to a scalp problem. Still in bra and panties, he went to their mothers room, put on the pageboy blonde wig and returned to his sisters room, and there he had the shock of his life.....

His sister was there.
 
As Gerald froze in shock, the next thing he saw was a flash from her phone she was holding. She was tall, with dark short hair, a fit build, and a small, smile. "Where are you heading Gerald?" She asked as he started to step up to him slowly. "Scurrying around looking for more clothes to steal?"
 
Gerald froze in shock, suprise and total embarrassment.....his sister wasn't supposed to be here for hours.....here he was, standing in her bra and panties, lipstick on his lips and their mother's wig.....could he look more humiliating?


"Uh.....nowhere sis," he stammered, his heart beating so hard you'd swear she could hear it.
"N-n-n-nowhere.....uh....your'e home early......I....uh, guess you're wondering why I'm wearing your underwear...."

Gerald wanted to crawl under a rock and die.
 
She stepped closer ti him. "Don't worry Gerald, it's okay. I know what your doing..." She said her tone lightening, her hands coming u0 abd touching his shoulders. "I know exactly what your doing.. and I think that it's perfect. I always wanted a sister!" She said stroking his shoulders. "You're going to be beautiful! I know it." She encouraged slash sge hugged him slowly. "I'll just have to post thus picture online-"
 

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