Part 3 Interactive Crossdressing story

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So here I am, in the kitchen making Matt a sandwich. My dress twirling around as I move across the kitchen. I might be dressed like a girl, but my culinary skills just aren’t that great. Stepping back and admiring my handy work, his sandwich looks like it’s been assembled by an animal.

“Sonya, take your time!” Matt calls down to me from the top of the stairs.

“Errr….. ok,” I reply slightly concerned.

Why does he want me to take my time? What is he planing? His reaction to me like this has been completely unexpected. I hope he’s not doing something stupid, like messaging our friends. As much as he is my best friend, I really don’t want him to tell anyone about this!

Grabbing the plate, I swiftly leave the kitchen and start sneaking up the stairs. I felt bad for not trusting him, but I honestly couldn’t live with myself if people found out. Wearing my sister's clothing was like my dirty little secret! People wouldn’t understand.

As I tiptoe and reach the top steps, I can hear Matt ruffling around. He’s no longer in my bedroom as the noise is coming from my sister’s room. Setting down the sandwich, I start creeping over to my sister's room door.

“Matt?” I call out as I gently push open my sister's bedroom door. “What are you doing?”

The door swings gradually open and an extremely embarrassed Matt stares back at me. His face bright red, like he’s been caught with his hands in the cookie jar. His shorts are crumpled on the floor as I catch him, sitting on my sister's bed, pulling up one of her pleated school skirts.

“Oh…..hey,” Matt blurts out as he freezes on the spot.

A little shocked, I point at the skirt he’s now wearing. Part of me was excited that he was dressing girly like me, the other part of me was concerned as to why he was.

“Matt?” I ask softly. “What are you doing?”

Matt finishes pulling up the skirt, smiles at me and starts wagging his finger.

“I hope you don’t mind,” he says. “I wanted to know what wearing a skirt is like and seeing as your dressed like that, I thought you would be ok with it.”

Matt starts moving around and twirling. My sisters skirt moving around freely as he does. I couldn’t help but let out a little laugh as I watch him.

“What?” Matt asks as he seems annoyed at me laughing. “I didn’t laugh at finding you in that dress!”

“No no….. it’s not that,” I reply “You just look so funny walking around like that.”

He stops, puts his hands on his hips and poses like a sassy girl.

“Are you trying to say I’m fat?” he jokes.

“No…..I’m trying to say you look stupid wearing a school skirt with the rest of your normal clothes. They don’t match.”

“Really?” He asks. “Do you think I should maybe……take your sister’s skirt off?”

This wasn’t a question I thought I’d get asked when I woke up this morning. Not only has my best friend caught me crossdressing, but he’s now crossdressing too. I didn’t want him to take the skirt off. I felt like he was doing it to understand me better.

“Nah,” I answer back as I move over to my sister's cupboards. “We just need to get you some clothes that go with that skirt.”

“Oh,” he stutters. “You want me to…… put more of her clothes on?”

Pulling out one of my sister’s flowery summer dresses, I hold it up to him. “Do you want to?” I ask as I take the red flowing long dress off the hanger and hold it up to him.

Using his fingers, Matt feels the material, of the dress, and pulls a face.

“I’m not sure about this,” he says apprehensively. “I mean, I like how airy it is down there, in this skirt, but to wear nothing but one of your sister’s dress….”

“It’s only a dress,” I reply as I push it into his hands. “Plus, you won’t be wearing just the dress. You can try on a bra too.”

Matt holds the dress up against his body.

“I’m not sure about this,” he says as he sits down on the edge of the bed. “Your family aren’t coming back anytime soon, are they?”

“I don’t think so,” I reply, rubbing my arm. “I don’t want them to catch me looking like this either, so if you're going to, best try it on now.”

Looking at me straight in the eye, I can see how nervous and uncomfortable he is.

“Should I try on a bra too?” he asks.

Reaching into her drawers and pulling out a lacey pink bra and throw it at him. He awkwardly catches it and as he moves, I, unfortunately, catch a glimpse straight up his skirt

“Dude,” I yell and avert my gaze. “Shut your legs when you’re wearing a skirt!”

“Man..., you looked up there on purpose!” Matt moans.

I don’t reply, I just roll my eyes at his suggestion.

“Ok…..ok, I will try this stuff on, but can you maybe give me some privacy as I change!” he says breaking the tension.

“You guna put it on?” I ask, actually excited that he’d decided to.

“Well, I will if you leave the room.” He answers as he signals me to leave.

“Okay…ok!” I laugh. “I’m leaving! If you need help with the bra, let me know.”

“Get out of here Sonya!” he moans once more.

I stand outside the room for about ten minutes. The sandwich I made looks lonely and I have to fight the urge not to eat it! I start reaching for the plate and as I do, the door creaks open.

“Err….” Matt says through the crack in the door. “I’ve put on the bloody dress.”

“Let me see!”

Matt slowly opens the door. His face is just as red, like a tomato. He’d put both the bra and the dress on. I couldn’t believe he was doing it! I wasn’t sure if he was enjoying it or was just humoring me. Still, it was super kind of him not to just judge me, but to try it for himself!

“I feel a little…..dirty,” Matt says as he awkwardly pulls down the dress so it covers more of his hairy legs

“Dirty?” I reply as I look him up and down. He’s a little taller than me, so the dress doesn’t fit him as well, but it still looked ok.

“Yeah…. I’m wearing your sister's underwear. It feels all sorts of wrong!”

“You’re only wearing a bra,” I reply with a smirk. “It’s not like you’ve put her panties on too.”

He looks at me and pulls a sinister expression.

“Nathan,” He asks as he steps a little closer to me. “Are you……are you wearing your sister’s panties?”

He lunges at me and grabs hold of the bottom rim of my dress. I try to move away, but I’m not quick enough. Matt flicks my dress up like a naughty boy would do to a girl, and he catches a glimpse of the panties I’m wearing.

“Dude!” I huff as I flap my dress back down to cover myself! “Not cool!”

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.