Part 4 Interactive Crossdressing story

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“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?”

“Well… you,” he stops and his face turns bright red. “You….. kinda…. Look um… cute.”

“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 and 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 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 with disappointment to his side.

“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!”

Matt snaps his fingers, like the bright bulb of an idea has just turned on inside his head. A smile races across his face.

“You need a wig!” he grins. “My sisters got a long wig at home! I will rush over and get it.”

Still not impressed with his idea, I give out a very noticeable sigh.

“Come on Nathan!” he pleas. “Look at me right now! I’m wearing your sister's clothes and supporting you by playing along with your dress-up antics. Maybe you can do me a favor and be my pretend girlfriend!”

Annoyingly, he had a point. I let out another sigh.

“I guess you have been pretty cool about this,” I reluctantly admit. “Okay….. go get your sister’s wig and I will try my best.”

Matt brings his hand up again for a high five. This time I don’t leave him hanging. He smacks my hand with the same enthusiasm that was showing on his face.

“You better go change out my sister's stuff,” I say as I point at his skirt.

In a hurry, Matt got changed into his normal clothes and ran out of my house. Not even five minutes later, he comes barging back into my room clutching the wig he’d borrowed from his sister. Panting, like a dog, he thrusts it in my direction.

“Here,” he pants. “Put it on and let's go!”

I grab hold of the jet-black clump of messy hair he’d handed me.

“This is going to take me a few minutes to style,” I say as I shake it out as best I can.

The wig was long, I guessed it would go halfway down my back once on. I’d not worn a wig before, but I’d watch crossdressers on the internet do it loads. I remove my pink bow and place it over my real hair. The long back hairs cover my face and I franticly start brushing away.

“This going to take long?” Matt asks impatiently as he jumps onto my bed.

“Do you want me to look like a convincing girl?” I growl at him as I brush through countless hair knots

“Well yeah,” he smirks

After another ten minutes, I finally feel like I’ve got it under control. I’d styled in a fringe that covers one of my eyes. The rest of the jet-black hair cascades down my shoulder and back, completely straight.

“What do you think?” I ask nervously, not knowing how Matt would react. I wasn’t even sure how to react to the reflection I saw looking back in the mirror.

“Fuck!” he exclaims.

“What!?” I cry back at him. Feeling so uncomfortable and out of my safe zone, I could have thrown the wig at him.

“You look….. amazing!” he yells grinning ear to ear. “With that wig on, you don’t look like a boy at all! You’ve been completely replaced with a cute girl!”

His comments make my soul fizz with joy. I smile at him and playfully brush some of the hair from my face.

“Thanks,” I reply bashfully.

With a satisfied face, Matt looks me up and down.

“If you're going to be my girlfriend, we need to make some changes to your outfit,” Matt says leaving my room.

“What, why?” I ask in frustration as I follow him into my sister's room.

Matt doesn’t answer, he heads straight for my sister’s closet. Moments later, he stands in front of me holding a pair of dark purple Converse and a dark denim jacket.

“I think you should wear these,” he says as he passes them to me.

I give him a funny look. “Why?” I ask. “What's wrong with what I’ve chosen?”

“We are going to the skate park for our date,” Matt explains. “The Converse will be cooler than the flower girl dolly pumps and the denim jacket will look cool with your dress.”

“Ok, but how did you know my sister had this stuff,” I reply as I sit on the bed and remove my dolly pumps.

Matt rubs the back of his head and his gaze shift nervously from side to side. “When you went to make that sandwich, I had a quick look.”

I look at him confused. “Why? Did you want to wear this stuff yourself?” I ask as I finishing lacing up the shoes.

“Nah,” he answers. “When I first saw you in that dress.”

“Oh god!” I interrupt him. “This was your idea from the start!”

He gives me a sideways smile. “Yeah, please don’t be upset! This is my chance to finally seem cool.”

“Your chance to seem cool,” I mutter under my breath as I put on the denim jacket.

The jacket was a little tight around the shoulders. It was short, only reaching down to my waist, but he was right. It really did look good with the dress. I wouldn’t have put the two items of clothing together. The dress was very girly but the jacket and shoes gave me a bit of attitude.

Well, is this good enough for you?” I ask as flick my new long hair from out under the jacket.

“Umm…,” he says rubbing his chin. “A couple more things and you'll be perfect.”

“Really?” I ask getting a little impatient. “We don’t have long until my family gets back, if we are going to do this, we need to go now!”

“Okay..ok!” Matt replies as he holds up a studded black belt.

Matt moves around behind me and starts untying the satin sash that wraps around my waist. The sash was part of the dress and I really liked it, but before I could say anything, Matt had already removed it, allowing it to fall to the floor. He wraps the belt around me and stands in front of me. Doing up the belt tight enough to sinch in my waist, he looks up and smiles

“Yeah, I like that better than the girly ribbon.”

“Do you,” I reply sarcastically.

Looking at the clock in the room, I start getting extremely worried

“Matt, we haven’t got long! We need to go now so we can get back before my family comes home!”

“Let's go on our date then!” Matt cheers as he grabs my hand and leads me out of the room.

As he pulls me, hair fulls into my eyes.

“Please don’t call this a date!” I complain as I struggle to see what I’m doing.

Before I know it, we are standing out front of the house and Matt has closed the door behind me. I’d never been out of the house dressed as a girl and I was starting to feel extremely anxious about the whole thing. Every little thing I felt, from the gentle movement of my hair and dress in the wind to the feeling of the cold on my legs through my tights, was a stark reminder of the situation I now found myself in.

“Matt,” I say gently as he starts walking down the front garden path.

“What's up, Sonya?” He answers, putting emphasis on my girl's name.

“I’m a little worried about this,” I tell him as I fold my arms. “I’ve never actually gone out dressed like this and I don’t really know how to be a girl.”

Matt walks up to me and grabs my hand, forcing me to unfold my arms. His soft grip and reassuring smile make me feel a little better.

“Look,” he says softly. “You don’t have to do much, just do as the other girls do.”

I nod and signal for him to lead the way.

He starts pulling on my hand again as we start making our way to the skate park. We did have to stop at his house really quickly to get his board. Hoping no one would see me, I hid behind the bushes as he got it from the back garden.

We’d been to the skate park many times, but this was going to be the first time I was going as ‘Sonya’. The older kids at the park always give me and Matt grief. We aren’t the best skaters.

My nerves were shot as we entered the skate park and approached the other kids. Lucky for me, there wasn’t many around at this time in the evening.

It was just Barry and his girlfriend Lara. Even though it was just these two, Matt didn’t seem any less interested in showing me off as his new girlfriend. Has both Barry and Lara spotted us, he grabs my hand and starts holding it tight.

“Nathan,” he whispers in my ear. “If anyone asks, you aren’t from around her and we met at camp.”

“Gotcha,” I nervously answer back as I brush the hair from my eyes.

“Dude,” he continues. “Remember you are a girl! Let me do all the talking and you just stand around looking pretty!”

“Is that all I have to do?” I ask slightly annoyed that he only wanted me to make him look good.

“Yes!” He answers back sternly.

I brush down my dress as it flaps in the wind. I absolutely couldn’t believe I was here, wearing my sister's flower girl dress! If anyone found out it was me, I’m dead! I Squeeze Matts's hand tighter.

“Hey, loser!” Barry laughs as he stops himself still and puts one foot on his board. “Does your mummy know you’re here this late?” He jokingly mocks.

Lara giggles at his comment.

I look away and tut. This is going to be painful!

Lara then instantly notices me. She looks at me and smiles. This wasn’t a reaction, from her, I was used to. Usually, she treats me like I’m some weird little creep. I brush the hair out of my eyes as my face goes bright red as I notice her looking at me.

“I like your dress,” she says with an honest smile. “You look super cute!”

“Thank you,” I answer back blushing.

“I’ve not seen you around before,” She grins.

Matt interrupts and stands in front of me. “This is Sonya” he exclaims as he points back at me. “She’s my date!”

Barry starts belly laughing. He curls over as he chuckles loudly.

“You’ve got a girlfriend?” he asks mockingly. “No way, there’s gotta be something wrong with her!”

Lara turns to Barry and gives him a sharp look. “Shut up Barry. That’s not a nice thing to say to a young lady!”

Lara approaches me. Her short skirt flaps in the wind as she stands up from the bench she was sitting on. Her smooth, bare legs and her golden blonde hair, make me a little jealous as she walks. She was wearing a denim jacket, like the one Matt had made me wear. Now I understand where he got that idea from! She stands close beside me. So close in fact I could smell the sweetness of her perfume.

She playfully nudges me with her elbow. “Boys eh?” she jokes into my ear.

“Yeah… boys,” I nervously answer back.

“I’m glad there’s another girl here!” She whispers in my ear and grabs my hand. “It’s soooo boring just watching the boys skate around all night.”

Lara stats pulling me over to the bench. I look at Matt with a worried expression. He just shrugs back at me.