It was probably the strangest night of my life, but I'll never forget it.
It all began with a simple request on my part: I had an upcoming date. My first ever one, if I'm being completely honest. It was a bit embarrassing to have my first date at nineteen years old, but I knew there was one person I could go to with advice. One person who would never judge me, no matter what.
That person was, of course, my older sister Emily. She was the sweetest, kindest girl in the whole world, and I was so lucky to have her. Even I, young as I was, could recognize that much.
Emily was easy enough to find. She spent most of her time in her bedroom, watching movies and playing video games, amongst less family-friendly activities that I was sure she didn't know I knew about, but our walls were very, very thin.
"Emily," I said with the tone of a little sister who wanted something. She picked up on it right away, if the roll of her eyes was any indication.
"'Sup?" she asked casually, not taking her eyes from her computer screen. I wasn't a gamer like her, so it was all Greek to me, but I loved watching her eyes dance across the screen as she bit her lower lip in concentration. It was adorable.
Unfortunately, I didn't have time to admire it. I had business to get to.
"I have a date with a boy from my class tonight, and I have no idea what to do. This is all brand new to me," I explained as I plopped onto her bed and fell back onto the mattress, hands falling to my side. The sound of the springs in the mattress pushed intrusive memories of the sounds I'd heard late at night from this very bed through the walls, but I shrugged them off. I was used to intrusive thoughts about my sister's sex life. It was totally normal to have the thoughts, as long as I never acted on them.
As I fought off those thoughts, I didn't even notice that Emily had completely disregarded her video game and turned her chair around to face me. In fact, I didn't notice until I felt her weight on me as she straddled me, apparently eager for details. She didn't even need to ask.
"He asked me out after biochem," I muttered sheepishly. Honestly, I hadn't even considered him an option, but that was no surprise. I'd never considered any boy an option in my life. It just never happened. My parents swore I was a late bloomer, but my sister thought I was just in the closet. I honestly didn't know what I was. I just knew that I wasn't interested in that sort of thing.
She shifted on top of me, and I was amazed at how warm her thighs were against my hips. It was rather cold out, so it felt kind of nice.
"You're not wearing that, are you?" she asked, gesturing down my body from the neck. From where she was sitting I couldn't even sit up, but I knew exactly what she meant as she grabbed my shirt and pulled it up a bit for emphasis. The cool air felt strange on my belly, and I felt just the slightest bit uncomfortable in this position with Emily all of a sudden.
"I, uh, I hadn't even thought about what I'm wearing," I admitted. "I don't even know what it's like to go on a date, and I don't know who else to ask, so I came to you."
She scrutinized me a bit before leaning forward so that I could see her face. Her bright green eyes narrowed as she seemed to be searching for something in my own. I didn't know what to do, so I just stayed in place, squirming slightly underneath her. After what felt like forever, she finally nodded, seemingly satisfied. Standing up quickly, Emily grabbed my hand and pulled me up to my feet.
"First off, let's fix your outfit," she said, grabbing my shirt and pulling it up and over my head before I could even realize what she was doing. As I felt the shirt begin to tangle in my hair, I began to protest.
"What the -- you can't just do this without a warning, Em," I said sharply, even as she ignored my request and finished pulling my shirt off. I was suddenly far more aware of the cold breeze on my chest. Emily smirked.
"Might not want to let the girls free until at least the third date," she said slyly.
Blushing, I pulled my hands up to cover my nipples, suddenly self-conscious about how puffy they were and my lack of blessings in the size department. I didn't say a word. I was afraid anything I did say would just call attention back to my lack of breasts. I hadn't even thought of wearing a bra.
Emily either didn't notice my discomfort, or pointedly ignored it. I wasn't sure. Instead, I felt her begin to tug on my shorts. Now I was faced with a choice: either reveal my breasts to the world -- well, Emily, but I wanted to be dramatic. Sue me. -- or keep hiding them and let her reveal something even more precious. I squirmed slightly in place and hunched down, trying in vain to stop her from disrobing me further. Alas, it was no use.
I felt her fingernails scratch lightly against my thighs as she pulled my shorts down to my ankles and shoved me to the bed to get my feet off the floor. As soon as I landed, she pulled the shorts all the way off and threw them across her room.
"Em, what the fuck are you doing?" I finally managed, thankful that I'd at least worn panties. That didn't stop her eyes from settling on them, though, and it was all I could do to try to cross my legs and hide them.
"Cute underwear," she said approvingly, "but that wouldn't matter anyway, since he won't be seeing them tonight. Right?"
I wordlessly nodded as she turned and walked to her closet, rummaging around for just a moment. I should have gone for my shirt, or even my shorts, but I was paralyzed in embarrassment. She was my sister, so I shouldn't have felt ashamed to be basically naked in front of her, but after hearing her moaning softly into her pillow at night, the thoughts kept creeping into my mind, and it was even more intense now that I was so underdressed.
"Try this on," she shouted, tossing a fairly short green dress over to the bed.
I complied, eager to put something on over my nude body. The dress fit great, which surprised me. She was a bit curvier than I was, so I'd expected anything of hers to fit me like a child wearing her mom's t-shirt to bed as a nightgown.
As if reading my mind, Emily chuckled and explained, "I used to wear it in high school."
That made sense. I stood in front of her mirror to see how it looked, and I was pleasantly surprised. The dress hugged my hips and butt rather well, and it came just halfway down my thighs. All in all, it made my butt and legs look very nice. Unfortunately, it wasn't quite as effective for my small chest. I leaned forward to test it, and my suspicions were right. What should have been mega cleavage turned into one of those creepy downblouse videos from online. I quickly stood up before my nipples were visible again.
