My Sister Ivy Part 2

She continues to dress him like Alice In Wonderland. Enjoy

My Sister Ivy Part 2

With my sister knowing the truth about me, I felt a weight lifted from my shoulders. Like the sky parting after a long rainstorm. I guess I should have expected this sort of grace from her. Being my older sister, Ivy has always been looking out for me. I guess she just can’t break the habit.

“Ivy….,” I say, with a burning question on my mind. “Why are you being so nice to me about this? I expected you to hold this against me or something. I mean, your brother likes to dress like a girl. Don’t you find that weird?”

Still holding onto my shoulders, Ivy rubs them gently.

“Do you think I should be disgusted, or want to out you to our friends and family?” She asks, almost offended.

I can’t help but look down and away from her honest eyes.

“I just feel that way Ivy,” I admit. “I’ve always felt like there is something wrong with me. I mean, what teenage boy wants to wear dresses and heels.”

Lifting my face with a finger on my chin, her face lights up with a bright smile.

“You’ve clearly not been on the internet then,” she laughs. “I think you just need to reach out to like-minded people.”

“How’d you mean?” I question with curiosity.

“All I’m saying is,” Ivy continues. “It’s easy to find yourself alone when you don’t reach out to the people that understand you the most.”

“Like you?” I reply

“Yeah I guess,” she chuckles. “Good thing you broke my makeup head…..huh?”

“Yeah……..,” I answer, rubbing my arm nervously. “I didn’t do it on purpose y’know.”

“I didn’t say that,” she retorts. “I just saw my opportunity to bring this whole thing up with you.”

“Is that right,” I say rolling my eyes. “You had this planned?”

“Sure did,” she answers, giving me a devious wink. “I thought it would be better for you this way!”

Turning to look at my face in the mirror, I look at the fantastic makeup job she’s done. Much better than anything I’d attempted in the past. I usually ended up looking like a clown.

“I do love the makeup you’ve done,” I say, looking at her in the reflection of the mirror. “What do you mean this is better for me?”

Ivy stands up and places her hands on my shoulders.

“Well,” she says, pointing at the Alice in Wonderland style dress “This way when we dress you up and mom and dad see you, you can blame your transformation on me.”

“Ivy,” I say, unconvinced. “I feel like there might be something in this for you.”

“Well…….,” she says, clapping her hands together. “This way I get a model”

Nudging me gently on the shoulder, she giggles.

“If you think about it,” she continues, “It actually works out great for us both. You get to be made all pretty and wear beautiful clothing. I get a free model to do my looks on!”

“Deal!” I say, giving her a thumbs up in the mirror.

“Good,” Ivy quickly answers and starts gathering items around the room. “Right, stand up and take your clothes off.”

“Boxers left on?” I question, giving her a suspicious look. “Right…?”

“No way!” she replies, gesturing me to start taking off my t-shirt. “Boxers are frumpy. They will ruin the lines of your dress.”

As I start removing my t-shirt, I start hiding my body from her. Self-conscious about how skinny I am.

A few uncomfortable minutes pass as I get myself dressed. Ivy was allowing me to borrow under items for the look. Some of which I’d borrowed in the past. I didn’t want to tell her that though.

I think she was pleasantly surprised by how easy it was for me to navigate putting on a bra. I think she was almost impressed.

The bright white tights did cause a few issues, but Ivy showed me how to put them on correctly. Makes sense once you know how I supposed.

Next up was the lush blonde wig. With Ivy helping me get the fit perfect, She quickly brushed it straight and tied it back with a ribbon.

With some stuffing into the cups and my corset pulled tight, it was time for the dress. As I worked my body into the correct holes, Ivy zipped up the back.

Frantically moving around me and adjusting the fit, Ivy looked determined. The dress was extremely tight around my middle, but with the corset sucking my waist in, it fit pretty well. I was finding it hard to breathe, but Ivy informed me that was natural.

“Heels,” Ivy says, holding up the heels she’d shown me earlier.

With my sitting on the side of the bed, I watched Ivy slip the tight black high heels onto each foot. I could feel them pinching my feet, but fitting quite well.

“Take it easy,” Ivy says, holding out a hand to help me up.

With one swift movement, she had me up and onto the heels. Still clutching her tight, I wobble on the spot. This was the first time I’d worn heels and I knew it was going to take some time to get used to.”

“Ok,” Ivy says, looking up at me, due to the extra height given to me by the heels. “Walk heel…toe.”

With her holding my hands, like a toddler, she helps me take my first steps. One step at a time, I walk from end to end of her bedroom. With each step, getting more and more confident.

“Jordan!” Ivy giggles. “Are you moving your hips like that on purpose?”

“Yeah…..,” I reply with a wry smile. “Does it make me look more feminine as I walk?”

Letting go of my hands and allowing me to strut my stuff, Ivy can’t help but laugh out loud.

“I love it!” she howls. “Have you been practicing?”

Stopping still, dropping a hip, I strike a sassy pose.

“I have!” I reply confidently. “I often walk like this when I think no one is looking.”

“We are going to make such a great team,” Ivy cheers and grins.

Flicking hair behind my shoulders, I give her a playful wink.  Looking into each other's eyes, we shared another great moment.

“Right,” Ivy says, shaking her head to snap herself out of the moment. “We’ve gotta do the photoshoot.”

“Ok,” I reply. “Where do you want me?”

Reaching for her camera, she walks over to the window and looks outside.

“Nice day,” she comments, turning to face me with a smile. “I think we should go out to the woods.”

“The….w-woods,” I croak, with my confidence fading and my shoulders slumping. “I can’t go out there dressed like this!”

“Don’t be silly Jordan,” Ivy replies, grabbing some more bits around her room. “I’ve gotta get some pictures, overwise this outfit was a waste of time.”

Gently taking hold of my hand, she leads me out of her room. As I awkwardly walk in the heels, dread starts filling my mind. Mom and dad are downstairs and they are going to see me like this!

With hair in my eyes, gusts blowing up my dress, and heels pinching at my feet, we made our way downstairs. Although the dress, wig, and heels fit my body really well, I’d never felt so uncomfortable.

“Mom,” Ivy calls out as we reach the ground floor. “Come look at this look I’ve done!”

With my heart rate rising, mom steps out of the living and into the hallway. As she sets eyes on us both, her face scrunches up with confusion.

“Jordan?” she asks, scratching at her nose. “Why are you dressed like that?”

With her staring, I go bright red.

“He broke my makeup doll,” Ivy interjects. “So as punishment, he’s agreed to help me with some looks.”

“Oh,” mom answers, looking me up and down. “That dress actually fits you very well. I’m a little jealous of your figure son.”

With Ivy standing next to mom and looking back at me, they make me feel like I’m a circus freak.

“I know…right,” Ivy says, looking me up and down. “I was a little surprised at how feminine he looks too.”

Mom takes a few steps towards me. Brushing strands of hair from my eyes, she smiles.

“How you doing blonde?” she jokes.

“Okay…,” I reply with a voice crack.

“Wonderful makeup,” mom comments, as she looks at my eyes. “You’re getting really good Ivy. You'll have to give me a makeover soon.”

“Sure,” Ivy answers. “We’ve gotta go right now though. I’ve got pictures to take.”

“One of your needs to clean up that mess in the kitchen!” Mom commands, as she puts a hand on one hip. “Don’t think you kids are leaving that all on the floor. One of you needs to go clean it.”

As soon as those words leave my mother's mouth, both she and Ivy turn to face me and stare.

“Jordan,” Mom says with a stern attitude. “It’s your mess right?”

“I’m wearing heels!” I plea. “I can’t clean it!”

“Piffle,” Mom giggles. “Women have been cleaning in heels for generations.”

And with that, I found myself cleaning the kitchen floor, dressed as Alice in Wonderland.