Sissy's First Heels

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"Aww, sweety do you like the dress?"
Sandra was looking me up and down grinning. I immediately looked down in shame and stood their frozen. 'had she been filming me?'

"Here these heels are my sister's, but I bought them for her the other day so you can borrow them. Oh and also," she dropped the heels by my feet as she went back to the dresser. "Here." She threw me a pair of white thigh highs. "Try those on. Since you're a size seven in boys, those size nine heels should fit. Boy's and girl's shoe sizes are basically the same, there's just a number difference of two. You should try and remember that. Just add two and that's your shoe size, princess."

I didn't know how to respond. I was stunned. I really liked Sandra; she was always so nice to me and pretty beyond belief with great fashion sense and style. But this was just too much, I thought I was a boy and she was treating me more like a girl. I wanted to run and hide, I wished I had never run into Sandra, I wished I hadn't asked her out, I wished I had just eaten the tampon and avoided this embarrassment. I wished and wished, but there I remained.

"Ok Sandra," I finally relented. I sat down on her fluffy pink bed and began to put on the thigh highs.

"Oh darling, you're doing it wrong. You want to roll them up first then pull them up your leg. And those stockings are seemed too so make sure the seems face in like this."

Sandra got down on her knees and rolled the first one up my leg. Grazing her hand along my inner thigh at the end sent shivers down my spine, I felt my little prick begin to stiffen in my panties.

"See like that, now can you do the other one?"

"I think so."

With a bit of effort I got the other thigh high on, after which Sandra adjusted it so the seem ran straight up my inner leg.

"Ok now the heels, pretty. I think you can manage that on your own."

I picked one of the heels up and began putting it on. They were black velvet kitten heels, maybe three inches, with thin black ankle straps. I hadn't looked Sandra in the face since she brought them in, but I could tell she was ecstatic. 'Is this what she wants? Does she like me as a girl or is she making fun of me?'

Soon I had both heels on and I looked down at myself sitting on the bed. As far as I could tell I looked like a girl, a flat chested one but a girl none the less. I peered up at Sandra for the first time since she had returned. She was grinning still, eyeing me up almost hungrily. 'Maybe she does like me as a girl. Or maybe just in girl's clothing?'

"What do you think," I asked timidly.

"What do I think? I think you're a hot piece of meat dressed like that. You'll make the boys go CRAZY walking home. Definitely a look. Now come on we need to get you going. My parents will be home soon and I'm technically not allowed to bring boys home, though they might not be able to tell with you dressed like that."

My heart sank again. I didn't think I was gay, in fact I thought I knew I was straight, but Sandra clearly had me pegged as liking boys even though I had just asked her out earlier that day. But before I could get any words together she grabbed my hand and started leading me to the front door. I stumbled and struggled to walk in the heels as Sandra gushed about my new femme appearance.

"I always new you'd look great in girl's clothes. You have a very feminine body type and soft facial features. You'd look even better with make-up. And maybe a wig and fake boobs too. I was surprised when you asked me out because--I mean, well, let's just say I'm glad things seem to be working out." We reached the front door and Sandra opened it. "We should do this again. Oh and you can swing by here after school tomorrow to drop off the clothes." I gingerly stepped outside, looking around and seeing nobody nearby. I turned back around to say bye to Sandra and as I did I saw her snapping a photo of me on her doorstep. "Bye bye Noel," she said in a teasing voice. "or should I say Noel," changing to the feminine pronunciation of my name before she closed the door in my face.

I stood there dumbfounded for a moment. When I turned back toward the street there was an older man walking by staring at me. He quickly averted his gaze as soon as I looked at him though and kept walking. I felt tears welling up in my eyes. I moved as if to run home but forgot I was in heels and tripped and fell, scraping my palms and dirtying the knees of my pristine white thigh highs. I burst into tears on the ground and turned again to face Sandra's house. To my surprise I saw her again, this time through her window. She was taking more pictures of me! We made eye contact briefly and she smiled before closing the curtains and disappearing. Still sobbing I got up and started wobbling home in my dress, stockings, and heels.

By the time I reached my home I had gotten the hang of walking, but I also realized my dad had gotten home early. I snuck around to the side door where I took off my heels and held them. I honestly figured my dad would catch me sneaking in like this considering how the rest of the day went, but I managed to get up to my room without being noticed. There I changed, hid Sandra's clothes, then snuck back out before re-entering as if I had just arrived. I made some small talk with my father before heading back upstairs. A few hours later I got a text from Kyle:

"Hey bitch, wear those panties to school tomorrow if you know what's good for you."

"Fuck," I said to myself. I had left them at Sandra's house.

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