Sonya’s Story

A Crossdresser’s Tale

Thinking he has the house to himself, Nathan gets himself quickly into his sisters flower girl dress. Being so very pleased with how well his sisters dress fits him, he doesn’t hear his best freind Matt enter the house. Being caught, Nathan expects the worst! What he doesn’t expect, is a serious of events that will change both of their lives!

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I could see Matt was holding back the laughter. I guess he didn’t want to upset me. I decided to take control of the situation, rather than leave this hanging in the air.

“Yeah, I’m wearing her panties,” I mutter annoyed. “What does it matter? I mean, I’m wearing all her clothing because I like looking like a girl!”

Matt doesn’t respond. He just brushes past me and reaches for the sandwich I made. Taking a big bite, he turns to me with a mouth full.

“I have an idea!” He blurts out. Food flying from his mouth as he does.

“Sonya,” he says with his mouth still full. “Think about what I’m going to ask you before you answer…ok?” He asks swallowing down his bite of the sandwich.

Pushing my hand into my hip, like I’d seen women do on the TV, I strike a sassy pose.

“What is it, Matt?” I question with a feminine attitude in my voice.

“Well…,” he pauses and points at my dress. “You know how you’re dressed like that?”

“Yeah?” I answer sarcastically

“Well… you,” he stops and his face turns bright red. “You….. kinda…. Look um… cute,” He continues, as he looks away blushing

“You what?” I ask abruptly.

I was utterly taken aback by his comment. I mean, I want to look cute and that’s amazing that he thinks I am, but he’s my best friend. I absolutely think it’s weird for him to be calling me cute!

“I….” he stutters. “Please don’t think I’m attracted to you or anything!”

“You just called me cute Matt!” I exclaim as I take a step back from him.

“I know!” he says looking down at the floor. His face was still bright red with embarrassment. “Will you just listen to my idea?”

“What Idea?” I uncomfortably ask.

“Well, you know how the kids at the skate park are always calling us losers?”

“Don’t remind me,” I answer with a gloomy tone.

“They are always saying we will never get girlfriends…… right?” Matt states as I see the embarrassment disappear from his face and his eyes fill with excitement. “I thought, with you dressed like that, we could go down to the skate park and you can pretend to be my girlfriend!”

Matt puts his hand up in the air, expecting me to high-five on his idea. Usually, I would, but this idea……I wasn’t so sure.

“No way!” I cry “They’d know it was me dressed like this straight away! They’d bully us for sure!”

“Why would they?” he asks as his raised hand fulls to his side, with disappointment.

“Matt, you knew it was me, didn’t you!” I explain. “You may think I look cute, but it’s still pretty obvious that it’s me in a dress!”

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GenderPlay Stories: Year 1 Collection

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Family Friend Makeover