My Stupid Sexy Sister

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.

Before I could protest, Emily had grabbed my hand and pulled me closer to her, kissing my cheek.

"You look great," she said. "Now put on those shoes I put at the foot of the bed and come down to the kitchen in about twenty minutes, okay?"

Confused, I nodded. What was she going on about? I slipped her shoes on and sat on the bed, fiddling with my phone while I waited for twenty minutes to pass. After a few minutes, I got bored and decided on a whim to go ahead and go my makeup. There was no harm in some cute pink lip gloss and some basic eyeliner. I finished it up with a bit of blush to make my freckles stand out a bit less. When I finished, I made my way downstairs and into the kitchen. As soon as I opened the door, Emily called out, "Hold on! It's not ready!"

I stopped immediately.

"What are you up to?" I asked, shifting uncomfortably in the green dress and matching heels.

"You'll see," she called out. "Go on to the dining room."

I did as she said, making my way to the dining room and sitting at the table. As I was reading an inappropriately lewd post on Reddit, I heard the door to the kitchen open. I sat up straight immediately and turned to face my sister. She was carrying two wine glasses that belonged to our parents and -- to my surprise -- a bottle of wine. Our parents didn't drink wine. Where had she gotten it?

"Goddamn," she said, looking at me intently. I felt a blush creeping up my chest and neck. "I figured a practice date would help you know what to expect tonight."

I nodded wordlessly. It made sense. I'd seen this trope in movies and TV shows, but never between sisters. It was usually a romcom trope that ended with the couple getting together. Like the scene in Wedding Singer. Well, it was worth a shot.

As Emily opened the bottle and poured the wine, she placed a glass in front of me and one more in front of herself. Sitting in the seat beside me, she rested her head dreamily onto her hand and smiled at me.

"Dinner is almost done," she drawled sultrily. "In the meantime, tell me about yourself."

I giggled awkwardly, unsure what to say. Ignoring my silence, Emily kept talking.

"You look beautiful, by the way," she said, eyeing me hungrily. She was really getting into the role. I should have expected as much from a Theater major.

"Thank you," I managed, pointedly ignoring the flustered feeling building up in my chest. Luckily for me, a timer in the kitchen went off, so I was looking forward to a moment to collect my thoughts and composure.

"Be right back," she said, grabbing my hand and kissing it. Perhaps it was my imagination, but I could have sworn her eyes lingered on my chest just a bit longer than they should have. I didn't even think of my probably-visible nipples.

She returned shortly after with two plates in hand, each with a delicious serving of chicken breast, mashed potatoes, and mac n' cheese. My favorite. We ate in relative silence, even as Emily kept asking me questions she already knew the answers to as my sister. I answered, doing my best to pretend she wasn't who she was, but it still felt a bit talking about my family to my sister as if we were on a date.

Before our plates were clean, I could feel the wine taking effect.

"...and then -- and then, I threw the rock and it completely missed!" Emily finished her story with glee. My head was getting just a bit swimmy from the alcohol, so maybe that's why I laughed as hard as I did, but as we held each other's hands and laughed outrageously loudly, I could see a twinkle in her eye. An unfamiliar twinkle. I let me gaze lead my attention down her face and to her lips, where I noticed a bit of cheese from the dinner.

"Hey, Em, you have a little, uh," I began, deciding to just go all in, reaching up with shaky fingers to rub the food from the corner of her mouth. I'd thought it was my imagination, but I'd have sworn in the moment that the way she'd licked her lips after that had been because of me. Before I could pull my hand away from her face, she grabbed it with her own and smiled at me.

"You know what comes next in the date, right?" she asked with a mischievous glint in her eyes.

I shook my head. I was having a bit of trouble thinking straight, but what else could there be? She'd helped me pick my clothes, we'd had dinner, and we'd talked and laughed together for hours. What else could possibly happen on a date?

As her smile morphed into a smirk, she leaned in closer and closer to my face. I felt her warm breath on my lips as our eyes met, and I finally recognized the look on her face. It was lust.

Part of me wanted to jerk back immediately, but another part wondered if this was the look on her face when she was pleasuring herself at night. Suddenly it was very easy to match up the sounds of her soft moans with this very expression. I stayed still, unable to force myself to move closer or farther. I had to leave the ball in her court. I trusted her to do what was best. I wanted this so badly, but I knew logically that I shouldn't. If I could let her make the decision, it would be way easier than forcing myself to.

After a moment of searching for something in each other's eyes, she finally closed the distance. Three inches apart. Two. One.

Our lips met and it was clumsy, with our teeth banging together softly and awkward giggles throughout, but it was my first kiss and I loved it. I loved it so much that I wanted more. More than any little sister should want.

Glancing over, I finally realized that the entire wine bottle was empty. When had we drank so much?

As I felt her hands caressing my arms and back, I realized that I really didn't care. All I cared about was being as close as humanly possible to the girl in front of me.

Our kiss grew more and more intense as we stood, knocking the chairs over in our lust-ridden clumsiness. Our lips didn't part for more than a second as our chests pressed together, followed by our bellies getting as close together as we could manage. Part of me wanted to curse her beautiful breasts because of the discrepancy, but another part of me wanted to do other things to them.

Even as our upper bodies were as close as they could possibly be, I found that I wanted that closeness everywhere. There was a blush creeping from my cheeks to my neck to my chest to my belly and -- finally -- to my pussy. I wanted her to touch it. With her hands, her own pussy, her tongue, I didn't care. I just needed her to touch it. To touch all of me.

"Let's --" I said as I gasped for breath between kisses. "Let's go to -- your room!"

She nodded grabbing my hand and -- to my dismay, pulling away from me to lead us to her room. It was the longest thirty seconds or so of my life, and my body felt uncomfortably warm as we clumsily stomped up the stairs and to the door. Before we could open it, Emily slammed my back into the door, kissing me hungrily once again. Her hands were holding my own against the door on either side of my head and I loved it even as I impatiently begged her with my eyes to open the door and let us into her room.

She relented and let go of my left hand, reaching for the knob and opening the door, but our lips didn't part until we got to her bed, where she pushed me forcefully onto the mattress. The springs sprang once again as they did most nights when she pleasured herself, and the thought that now I would be the one pleasuring her filled me with a bubbly warmth.

She straddled me, much as she did before, but this time it was different. The context was different, the look in her eyes was different, and both of our desires were far different. She trailed her finger down my chest, running it briefly over my left nipple. I let out a soft moan as I longed for the touch to return, but her finger just kept getting lower and lower before settling onto my hip.

Changing her position, she put her right leg just between my own legs and I realized that no matter how close we got, our clothes would still be in the way and that infuriated me.

I eagerly reached up and pulled her shirt off, struggling a bit to get it over her head because of her ponytail, but when I did I threw it across the room as she'd done with my shorts earlier. Emily smirked as she noticed my gaze on her beautiful breasts, and her smirk intensified as it took me an embarrassingly long time to unfasten her bra.

As I reached up to caress her breasts, Emily suddenly turned serious. Despite the fact that we were both clearly tipsy, she refused to let me go further no matter how much I wanted to.

"Are you sure?" she asked, looking into my eyes and pulling away every time I tried to kiss her. I groaned in frustration as my lips longed for hers.

"I am," I insisted, struggling to pull her closer. She nodded to herself and the smirk was back.

"Trying to seduce me on the first date is rather bold," she said sultrily, standing and getting just out of my reach. I sat up and tried to protest, but she put a finger to my mouth before I could speak. "I'll allow it, but only if you obey my every word."

That was a suggestion I'd have been wary of at any other time, since she was my older sister, but this time I was desperate. I would do anything if it meant I could have all of her right now. She crossed her arms, pushing her large breasts together in the most appetizing of ways.

"First," she said, lifting a leg and -- with her sneaker-clad foot -- pushing me back onto the bed. "I want to undress you. Right this very moment. You aren't to help me; I want to explore your body all on my own."

I nodded as she crept closer, pulling the skirt of my dress slowly up my thighs and rubbing her nail against my left thigh as she did it. The light scratching sensation was driving me wild, and I could only imagine those seductive hands going elsewhere. I closed my eyes in bliss and let out a soft moan.

"Someone's eager," she drawled, pulling the dress up to my waist and linger just a bit longer than was necessary over my panties. As her fingernail caught the bottom of them, I could feel the fabric rubbing more tightly against my tingling pussy. My body spasmed a little of its own accord as my breathing quickened. This was getting ridiculous.

"Please, fu-" I began, but she shushed me and put her finger over my lips once more.

"You can talk when I tell you you can talk," she said harshly, and it was the hottest thing I had ever heard. I nodded meekly, swallowing a mouthful of saliva. My legs squeezed together as my body tried to create some sort of friction for my aching pussy. Emily just giggled at my efforts.

After the longest eternity of my life, she pulled the dress up over my head and stared at my pathetic breasts hungrily. I'd never imagined that someone could want them like this, but it felt good to be desired. She rolled the dress up in a peculiar way, and I waited for her to toss it aside, but instead, she grabbed my hands and flipped me over onto my belly. Pulling my hands behind my back like a cop would do to a criminal, she used the dress to tie my hands together.

When she flipped me back onto my back and I sat up, I stared into her eyes pleadingly.

"Speak," she said. "But only address me as your mistress."

Another jolt of pleasure shot down from my burning cheeks to my groin as I nodded.

"M-mistress, please fuck me," I begged, and my eyes were watering from unfulfilled lust. She smirked once more and sat down beside me, kissing me on the lips. Just as I was getting into it, however, she pulled away, giggling cruelly.

"Do you think you deserve to be fucked by your mistress?" she asked, trailing her infamous nail down my neck and to my left nipple. Part of me was jealous that I was down to my panties and she wasn't, but I didn't dare speak my concerns. I was too focused on the light caress of my puffy pink nipple by her gently finger. Even as I fought back another moan, she leaned in closer and gave my nipple a playful bite.

"Oh God," I moaned. "Please, mistress, I'll do anything."

It was a rash promise, but I didn't care. I just wanted the teasing to stop. I wanted to cum, and I wanted her to be the one to do it to me. My fingers grabbed the blanket tightly as I felt her tongue touch my chest and work its way up to my nipple. It was so soft, but also coarse enough that my nipple was being overwhelmed with pleasure. If she kept this up, I would orgasm just from nipple play, but that wasn't enough. I wanted her elsewhere.

"You have been rather well-behaved, my pet," she whispered seductively. Being called her pet should have been demeaning, but it just made me tremble even harder.

To my immense relief, her fingers went for my panties, peeling them off slowly. I eagerly lifted my ass from the blanket, desperate to get them off so that she could do anything and everything she wanted to my entire bottom half. As she pulled my panties lower on my legs, her tongue followed from my upper thigh to my lower thigh to my knee to my calf and -- at last -- to my feet. As the panties were fully removed, she also pulled the heels off, kissing my toes gently.