A young man receives assistance from his sister when he is caught cross-dressing.
Chapter 1: Sisterly Encouragement
I couldn't help myself. I'd always been fascinated with women's underwear. The idea that they caress a woman’s most intimate area has always turned me on. I knew that it was weird, even borderline fetishistic, but I just couldn't ignore the thrill it brought me. I was ready to turn it up another notch.
I crept into my sister's room feeling like a criminal. The late afternoon sunlight shone through her bedroom windows as I checked each dresser drawer until I found what I was searching for. Silky, soft panties, bras, and other lingerie pieces greeted me with an alluring charm that was impossible to resist. I picked up a pair of her satin bikini panties and held them to my nose, inhaling the scent of clean women’s underwear.
I couldn't explain why, but the scent of her clean panties made me feel closer to her, and for some reason, more aroused. I looked around her bedroom and saw a picture of her and me on the wall. I felt slightly guilty for breaking her trust, but the intense lust pushed me beyond logic and rationale.
My dick was rock hard, sticking out in front of me while my sensitive nipples ached. I had never gone so far before. I had plenty of intimate women's clothing, but I had bought all of that online, at department stores, and even thrift stores myself. I had never gotten my hands on panties actually owned by a woman before.
I set the stretchy black satin garment on her dresser and pulled off my t-shirt, now standing completely naked in my little sister's room. I rubbed and pinched my stiff nipples, letting out a quiet groan as my cock throbbed.
I stepped into her panties and gasped as the soft, smooth fabric embraced my ass, cradled my balls, and hugged my rock-hard cock. The sensations seemed more intense than when I wore my own panties, and I imagine it was because they belonged to my sister this time. The feeling of the soft fabric pinning my erection against my body made my head spin.
I couldn't believe how aroused I was. I pulled a pink sports bra out of the drawer, examining it closely before pulling it over my head and maneuvering it into place. The tight bra hugged my upper chest and pressed against my hard nipples. I took a deep breath and let it out slowly, staring at my reflection in the full-length mirror on the back of my sister’s closet door.
I had never really looked at myself looking so feminine before. I turned to the side, looking at my plump curves, my soft belly, my big round ass squeezed by her shiny panties, and my breasts small but noticeable due to my weight. I really wished I had Stacy's big breasts just to know what it felt like.
I examined my reflection in the mirror and sighed. I had to control myself, but I wanted more. I found one of her satin bras and wondered what it would look like on me. The cups would be very empty, used to housing her enormous breasts.
I would have given anything to have her body and her assets. My younger sister was a full-figured, curvy young woman, and I admired her body in so many ways. I envied her heavy breasts, her wide hips, her thick thighs, and her beautiful face. I wanted to be her, I wanted to know what it would be like to be in her body, if only for a day.
I sighed again, letting my hands trace their way around my own curves. I knew it was my ass that fueled my desire, as it was the only feminine shape I had to my own body. I was overly fascinated with my own backside. It was big, round, and shaped like a woman’s, that was for sure.
I took notice of the way her panties hugged my crotch tightly, squeezing my erection. My eyes glanced at the clock on her bedside table. It wouldn't be too long until she'd be back from hanging out with her friends, but I felt like I had plenty of time to enjoy myself in her room.
I wanted to know how it felt to have real breasts, big, heavy breasts like my sister, and I'd tried to simulate the feeling with padding and even water balloons inside my own bras before. But I knew it was nothing like the real thing.
I looked at myself once again, running my hands over my body, feeling the soft fabrics over my skin. I reached down to squeeze against my erection through my sister's panties, breathing in deeply as I did. I slowly began to rub myself through the front of her panties, my cock head poking its way out just enough for me to feel it along the elastic of the panties.
I closed my eyes, once again imagining myself with a big, bountiful chest, my hands cupping them as I felt the weight of a woman's curves as my own. My breathing got heavier and heavier. I started to moan and whimper softly with pleasure. I rubbed my hard nipples through the soft cups of Stacy's bra, causing shivers to run down my spine. My hand gripped my dick tight as I squeezed even harder, getting carried away in my fantasy.
I tried even harder to imagine myself with breasts like Stacy's. Two enormous, round mounds that filled my hands perfectly. I imagine myself squeezing them, kneading them, playing with my hard nipples and feeling their weight and softness.
I started to rub my nipples and my pulsing cock faster. My moans became louder and deeper as the image in my mind became clearer and more vivid. I could feel the satin sliding against my ass as I moved my hips back and forth in front of the mirror.
My cock was profusely leaking pre-cum. I reached down to grab one of Stacy's vibrators, hidden away in her underwear drawer. I slipped it into my soaked panties, pressing it against the base of my needy cock. I gripped the mirror frame tight, my knuckles turning white as I watched myself in the mirror. I was a mess of moans and gasps as I felt the vibrations on my dick.
My cock was throbbing, begging for release. I closed my eyes and pictured myself as a woman, my delicate nipples pressed against the fabric of the bra as I rubbed my pussy.
I pulled the vibrator out of my panties and positioned it directly on the head of my rock-hard dick. The vibrations coursed through my body like lighting, sending waves of pleasure pulsating through my nerves. I moaned loudly as the pressure built in my balls, every muscle in my body tensing up tightly as my climax approached.
My hand shook as I pushed the vibrator harder against my swollen head. I felt my cock twitch and heard a gasp behind me.
My eyes snapped open, and I saw Stacy standing in her bedroom doorway, frozen in shock. Her mouth hung open, and her beautiful blue eyes were wide with surprise. Her stare bore into my soul like a hot poker, and I swear I could feel the heat of it against my skin.
She couldn't tear her eyes away from what she had discovered. Her gaze swept up and down, taking in every inch of me with her gorgeous eyes.
"What the fuck, Nick? What perverted shit is this?!" She exclaimed, unable to hide her shock.
I froze, the vibrator still pressed against my straining cock. I felt my heart race, a mix of panic and embarrassment flooding my senses. "Stacy, I..." I stammered, trying to come up with some excuse, hoping that I would wake up from this nightmare.
"You dumbass!" she exclaimed, her hands flying to her hips, "What on earth are you doing wearing my underwear? And are you really using my vibrator like that?" She asked, her eyes narrowing, a bewildered half-smile appearing on her lips.
I was frozen, speechless, and I just couldn't believe it. My little sister saw me, and she wasn't calling the cops or screaming bloody murder. On a strange impulse, I took a step towards her, the vibrator still pressed tight against my leaking cockhead. A shiver shot up my spine as the vibrations moved down the shaft, firing through my balls. She tilted her head and shifted slightly, looking me up and down with curiosity and wonder in her eyes.
Her gaze lingered on my soft, plump figure, as well as on the tight sports bra and shiny panties I had on, her own underwear clinging to my ass. "Nick, I know you like to dress up, but I never thought you'd put on my clothes. How many times have you done this before?" she asked, a soft smile starting to form on her lips.
I swallowed hard, my heart pounding as I looked at her, still holding her vibrator against my throbbing cock head, leaking copious amounts of precum down and saturating the front of her delicate panties. "St… Stacy," I stammered, "Never… I... I didn't mean to..."
"My ass," she growled, stepping closer to me, "You snuck into my room and put on my bra, my panties... That's just so perverted, Nick. I can't believe my own brother would do something so... so naughty." She glared at me with her fiery eyes glinting in the late afternoon sunlight.
I shivered under her gaze. She moved towards me, snatching the vibrator from my shaking hand. The vibrations still rang through my body and my cock twitched at the sensation.
"So, have you been fantasizing about my big tits? I know you stare at them all the time. I thought it was a typical guy thing cause boys can’t help but ogle a pair of big titties. Now I think it’s because you wish you had your own pair, am I right?"
She pulled the panties up so they covered my cock completely, wedging the back between my big ass cheeks. She pressed the vibrator firmly against the head of my cock through her panties, sending shockwaves of pleasure through me, and I moaned, unable to hold back. The sensation was mind-blowing. She pressed harder, the vibrations moving through to my balls, sending a shiver up my spine. My hips involuntarily bucked forward, and she let out a giggle.
"I never realized you were such a horny bastard, Nick," she whispered in my ear. "You're such a naughty big brother." She grabbed my hand and mashed it against her heavy breast, pressing it into her flesh. She kept the vibrator pressed down on the underside of the head of my cock, causing me to tremble in place.
I could feel every inch of my cock being enveloped by her satin panties. My sister's hand was on top of mine, pressing it firmly into her big breast. I couldn't believe what was happening. The mix of shock and excitement ran through my body and settled right in my groin.
"That's it Nick, cum in your little sister's panties," she whispered in my ear, her breath hot on my skin.
The pressure of her hand, the vibrations of the toy, and the feeling of her breast spurred me over the edge. I moaned out loud as I felt my balls tighten and a new surge of pleasure burst through my aching cock. It throbbed as my balls boiled with cum, sending hot ropes of jizz jetting out of the pulsating tip, filling her panties with the single biggest load of my life. My legs trembled as I unloaded, my breathing ragged, gasping for air.
"Oh fuck, Stacy, I… I'm sorry!" I stuttered, my heart racing as I looked at her in complete shock and amazement.
She pulled the vibrator away from my pulsating, oversensitive cock and turned it off. "What are you apologizing for, Nick? You obviously loved every bit of this," she murmured, biting her lower lip as she looked me deep in the eyes. "Just look how much you soaked the inside of my beautiful panties, defiling them with your cum."
She pressed her body to mine, her soft hands moving to gently caress the sides of my face. Her blonde locks fell down on her shoulders, brushing against my skin. I could smell her vanilla body spray, mixed with the aroma of our bodies, mingling together.
"You wanted that, didn't you? You craved an orgasm while feeling your sister’s panties against your skin." Her voice had gentled, and I could tell that she wasn't actually upset. I looked down at her and nodded softly, unable to speak. She leaned in close, pressing her full, soft breasts against me.
"I knew you had to cum before we could talk about all of this. There was no way you were going to be rational with that throbbing cock telling you want to do. So, how do you feel now?" she asked, holding me close, gently cradling my face with smooth, soft hands.
"I feel like a perverted big brother," I said softly.
"Don't worry," she replied, gently rubbing my cheek, "I'm not mad at you. I just think you need to understand how to channel your feelings and desires. You don't have to feel guilty for wearing my clothes or liking women's underwear. It's just an extension of your personality, and I love you no matter what."
She leaned in and kissed my forehead softly, her scent gentle and alluring. Her words comforted me, and I smiled meekly up at her as my cock twitched inside the cum drenched panties.
She raised a perfect eyebrow and shook her head slightly. "That wasn’t enough? Well, why don't we make sure your needs are taken care of completely before we talk about why you snuck into my room. Come with me," she demanded, grabbing my hand and tugging me out across the hall and into the upstairs bathroom.
We hurried into the bathroom where she steered me over to the bathtub. She turned on the hot water and immediately began undressing. I was transfixed as I watched her heavy breasts bounce with each movement. Her blonde hair was disheveled, the strands hanging softly beside her round, pink cheeks.
"Nick, take my bra and dirty panties off," She put an extra emphasis on the word 'panties' that sent a shiver through me, causing my cock to stiffen again.
I was already sensitive with my recent orgasm, but the excitement built up within me and I felt my cock twitch. I nodded, standing frozen in front of her, with lust in my eyes. My hands trembled as I carefully peeled her bra over my head. Once off, I gently laid it on the side of the bathtub. I looked up and watched her reaction as I slid her cum drenched panties down my legs, freeing my still throbbing, and very hard cock.
Her eyes widened with delight at the sight of my erect dick. She let out a soft gasp and bit her lower lip. "You sure do like my tits, don't you?" she giggled, her eyes glowing.
My face flushed, but I nodded. I couldn't deny it anymore. I felt a shiver run through me as she reached out and grabbed my cock firmly in her delicate hand. Her soft, warm hand slid all the way up and down, already coated in my previous expulsion, pulling the hot, heavy skin of my dick, causing a shiver to tingle through my body. My heart raced as I marveled at the touch of her soft hand rubbing my slippery erection.
"Fuck! You are amazing. I haven’t had a woman do this to me in quite a while," I breathed out, my dick twitching in her hands, pulsing at her touch. Her fingers wrapped around my throbbing member and began to massage it deftly, in rhythm with her breasts jiggling in front of my face. I groaned as I felt my cock start to respond, twitching and jerking in her hot, wet hand.
"Touch my breasts, touch my body, explore me, feel me up. I want you to know what I feel like. I want to make you feel good." Stacy's voice was tinged with a captivating silkiness that seemed to soothe my nerves.
Her warm hand trailed down over the pulsating head of my throbbing cock, following with her magical fingers lower, treating me to exquisite pleasure. Her titties swayed gently as she leaned into me, offering me her plump globes. I eagerly seized them, moaning as I gripped her soft flesh, kneading them, as if trying to make her already ample mammaries even bigger in my hands.
Stacy leaned into me, encouraging my exploration. I gently brushed my thumb across one hard pink nipple and marveled at how she shivered under my touch, her breath hitching. I felt her other hand begin to squeeze my ass, making my entire body tremble as she brought her thumb gently over the head of my cock in controlled, firm circles as her fingers squeezed my throbbing shaft with just enough pressure.
A wave of lightheadedness washed over me. I'd always fantasized about what it would be like to be touched so intimately by a real woman. Even if that woman was my sister, I couldn't help but surrender to the mind-numbing pleasure of her incredibly skilled, soft hands.
Stacy's eyes bored into mine, challenging me to enjoy this as she started to knead and massage my ass. My hips started to buck and roll on their own, my cock searching for some release. I felt like I was in a dream.
"Cum for me big brother. Release yourself again. I want to feel you pulsing in my hand," Stacy begun stroking me with renewed vigor, forcing me to rapidly approach the edge of another explosive climax. My cock twitched and bounced in her hand as she pulled at me. Her grip felt so much better than my own, so tight but so gentle.
"Look at you, big brother. You're like a damn teenager. Already desperate for your next cum," she purred.
I dug my fingers into her plush tits and groaned as my back arched. My eyes went white and I exploded again, this time pumping a heavy load directly at my sister’s naked body. Each squirt of cum that left my cock forced a whimpering moan from me, tears gathering at the corners of my eyes. The wave of relief and pleasure it gave me only lasted a second before it turned to sheer exhaustion.
Stacy looked down at the mess on her belly, on her thighs, on her pelvis, then looked back at me, eyeing me with wild excitement. "Good job, Nick," she moaned huskily, her heavy breasts jiggling with each word she spoke.
My sister's lower body was covered in thick, white cum, and I was spent. I felt a great weight lift from my shoulders. She had shown me that my femininity wasn't something to be ashamed of but embraced.
I looked up at her and smiled sheepishly, "I'm sorry, Stacy."
"Don't be sorry, Nick," she said, her voice gentle, "but you can let go of my tits now."
I looked down and realized that I was still gripping my sister's heavy breasts, my fingers digging into her soft flesh, leaving red marks from the pressure. I quickly let go and backed away, blushing with embarrassment.
"Sorry," I mumbled again, "it's just that, um... I've never touched a pair of breasts like yours before. You made me feel good, really good."
She smiled at me and stepped into the bathtub, gesturing for me to join her. "Come on, we both need to shower. You got your cum all over me." Stacy giggled as she helped me into the tub. "You know, you don't have to be embarrassed about being yourself. I'm your sister, I love you no matter what. Besides, it's been a while since I've had a real live penis in my hand," my sister blushed at her admission.
She turned on the showerhead, the warm water cascading down on both of us. I reached for the soap, wanting to help her clean off my mess. I immediately began washing away the semen that had been plastered over her lower body, unintentionally letting my hands move closer and closer to her core without realizing it. My soapy hands traced the curve of her hips, moving over her thick thighs and gently caressing the soft tissue.
Stacy's entire body shuddered as I touched her; I immediately pulled back my hands. "I'm sorry, Stacy. I didn't mean to..."
She shushed me, silencing my apologies by placing a single soft finger against my lips. "You don't have to apologize, Nick. I know you're very inexperienced with women, and I also know you won't do anything I ask you not to. Go ahead. You can explore my body, just don't touch my pussy… yet." Her voice was soft and gentle, and I could see the understanding in her eyes.
I nodded and slowly brought my hands back to her body. This time, I made sure to avoid her plump mound, focusing instead on the rest of her curves. I washed the soap suds all over her breasts, over her soft tummy, down her strong legs, and finally finishing with her big round ass.
The entire time, she watched me with a small, sly smile on her lips. I could see the contentment and excitement in her eyes as I touched her. I was unable to take my hands away from her large butt, squeezing and caressing her fat cheeks in my soapy hands. A low moan escaped her throat, and I felt a stir in my crotch.
"Feels good, doesn't it?" she muttered, closing her eyes as I continued to massage her soft, round ass.
"Sorry," I murmured back, feeling my cock twitch in response. I wasn't sure if it was the sight of her soaped-up curves or the thought of exploring them further. But it felt so right.
"Please stop apologizing," she said, her voice soft and husky. Her eyes opened, and she looked at me in a way that sent chills down my spine. "I trust you. If you want to explore my ass, go for it." She turned her back towards me and bent over slightly, giving me full access to her luscious curves.
I swallowed hard and let my trembling hands move back to her ass once more. Her skin was so soft, glistening with moisture under the stream of water from the showerhead. My mind was racing, and I couldn't believe what was happening. I'd never felt so turned on in my life. My cock twitched as I traced the firm, round globes of her ass with my wet hands.
I squeezed them gently and felt a low growl rise up in my throat as I took in her luscious butt. I couldn't believe it, my sister was bent over in front of me, practically shoving her ass in my face. I gulped hard, trying to keep my hands from shaking as I explored every inch of her fleshy ass. I squeezed her sensitive flesh and ran my fingers along her crack, causing her to moan and wiggle her hips.
My cock had become a steel rod again, trapped between my thighs under the running water. I could feel the throbbing in my veins, begging me to stand up and plunge it into her asshole. I knew I couldn't do that, but I could let my hands wander a little bit more.
I parted her ass cheeks, revealing her tight little puckered hole. I felt my heart start racing with excitement and nervousness as I saw her pink rosebud winking at me. My cock throbbed harder as I thought about what it would be like to bury myself in that forbidden hole. I shook my head with determination. It's not right, I thought. I won't do that. But I couldn't help but fantasize about it.
"Do you like what you see?" Stacy asked me seductively.
I looked at her plump ass for a moment, and then I slowly began to caress her soft, smooth skin. I gently ran my fingers up and down her crack, lingering at her tight pink rosebud.
I heard Stacy gasp softly as my fingers moved lower, and she instinctively pressed her ass towards me, inviting me to touch her further. I hesitated for a second before allowing myself to follow that enticing invitation. I slowly traced my fingers along the outside of her hole, feeling it clench and unclench under my touch. I could imagine filling her ass with my cock, feeling every inch squeezed and teased as I thrust in and out.
"Nobody has ever paid this much attention to my butthole," Stacy whispered, her voice trembling.
Her body shivered as my finger lightly traced along her tight, pink hole. I hesitated, wondering if I should push the boundary further. I looked at Stacy standing before me, bottom tilted up, hips swaying slightly. I saw she was biting her lower lip, eyes closed. My senses spiked to new heights and a rush of excitement surged through me. I rubbed my slick finger in circles over her asshole. It clenched and relaxed again, and I felt her take a deep breath. I had been given permission and I wasn’t about to waste it. I pushed my finger against her anus and let my slick digit slide into her tight ass.
Stacy arched her back and let out a guttural groan as her butthole completely swallowed my probing finger. I could feel her sphincter squeezing my finger as I explored her backside, relishing the soft warmth that enveloped my digit.
"I think that's far enough, don't you?" she whispered.
I reluctantly removed my finger, her puckered hole relaxing and releasing my touch.
"Let's rinse off and then finish our talk," she said, moving us under the shower jets. The warm water cascaded down our bodies, washing away the soap suds. I took one last look at her curves before stepping out of the shower and wrapping a towel around my waist.
Stacy followed me, wringing the water out of her blonde hair and looking at me with a soft smile. She guided me to her bedroom and sat me down on the edge of her bed, her weight causing it to creak softly. She sat next to me, her thigh pressed against mine, and took a deep breath.
"Nick, I know you're struggling with your feelings right now, but I want you to know that it's okay. I want to help you with this as much as I can," she squeezed my thigh, "can you promise me that if I dress you up in some of my clothes that you won't ejaculate all over the place?" Her question caught me off guard, but I nodded my head eagerly.
"Good, now let's get started." She stood up abruptly, pulling me to my feet as well, and said, "I want you to pick out the things that make you feel the most feminine. What feels the best against your body, your skin." Stacy looked at me with a soft smile, expecting me to begin rummaging through her closet.
I hesitated for a moment, not knowing where to start. My heart was pounding in my chest. I glanced around at the multitude of dresses, skirts, and shirts hanging up, and then at all the different kinds of lingerie that filled her drawers.
“Can you just pick for me please? You’re a girl, you know what to do. Just, no lace please, it’s very uncomfortable,” I pleaded with my sister.
She decided on a tight, silky black dress that caught my attention immediately, and I reached out to touch the smooth fabric. My cock stiffened immediately and I bit my lip. I took the dress down from her hands and held it against my chest, trying to imagine what I would look like wearing it.
"I figured this would be to your liking," Stacy approved, smiling at me. "Let's see if it fits."
She led me over to her full-length mirror on the back of her closet door and held up the dress for me to slip into. As I stepped into it, my heart was pounding loud enough to echo through her room. I was wearing a dress for the first time.
"You need panties," she whispered into my ear.
I nodded. "Remember, no lace please."
"Of course. You need something that feels soft against that throbbing cock of yours," she chuckled.
"Right," I replied, my voice barely audible.
Stacy reached into one of her drawers and pulled out a pair of silky panties that would barely cover the sides of her generous hips. She handed them to me, and I slowly dipped my hand into the soft material, finding them deliciously warm and inviting.
"These should fit you well, just snug enough to press against you in all the right places, but stretchy enough not to be uncomfortable," she continued, her gaze burning into mine. "You wish you had a pussy like mine, don't you? To feel these soft, stretchy panties caressing a nice, warm set of lips between your thick thighs."
I blushed scarlet, aroused and uncomfortable at the thought.
"Well, that's enough teasing for now," she decided, brushing back a loose strand of hair and turning to look at my reflection in the mirror. "You look good in that dress, Nick." She spanked my big ass through the dress and I yelped.
My cheeks burned, and I looked at myself, surprised by how natural it felt wearing Stacy's clothes. The stretchy material slid easily over my legs, clinging to my hips, and stopped just above my knee. It was tight against my body but never constricting or uncomfortable. The dress hugged my figure perfectly, giving the illusion of curves where there were none. Stacy handed me a matching push-up bra, and I hesitated, biting my lip nervously.
"Put that on, I have to make a call. Don't jizz in my panties this time... at least not yet." She spanked me again before stepping into the hall, completely naked, to make her call.
I adjusted the bra and panties until they fit just right, each inch of soft silky fabric clinging to my body, accentuating my nonexistent curves and creating an illusion of femininity. I smoothed down the front of the dress, admiring how it molded to my slightly chubby chest and wide waist.
I sighed contentedly as I stared at my reflection in the mirror, taking in every detail of my makeshift disguise. I looked closely, wondering what it would feel like to have a woman's body. What it would feel like to have large, heavy breasts, to have wide hips, and have my aching cock and swollen balls replaced by a soft, flat plane between my thighs.
I bit down hard on my lower lip as I tested the straps of the bra, trying to imagine my reality shifting. I reached down to adjust the waistband of the panties, feeling the soft, silky fabric rub against my cock, making it throb even harder.
I heard Stacy’s voice, beckoned through the open doorway. She stood there, her naked body glowing in the dim lighting, a phone in her hand. “Ready to feel like a real woman tonight?” she asked with a sly smile on her face.
Her question snapped me out of my reverie, and I tried to gulp down my anticipation. "Yes," I croaked out, my throat suddenly dry.
Stacy stepped closer to me, her eyes fixated on my face. "Mmm... I see that you're already getting excited, big brother. It's sweet," she purred at me, her voice dripping with suggestiveness. "Now tell me, how do you think it would feel to be like me? Would you enjoy the sensation of wearing silky stockings and high heels, or perhaps a tight corset that accentuates your curves?" Stacy asked, moving closer to me. She leaned in to press her bare breasts against me, her nipples hardening against my dress-covered chest through the bra I had on. I felt my cock twitch and strain against the panties I was wearing.
"I... I don't know," I stammered, unable to tear my eyes away from her tantalizing body.
"With a little practice, you'll find out," she whispered seductively.
As if to demonstrate, Stacy sashayed past me, her hips swirling with a hypnotic rhythm. She walked over to her vanity and picked up a pair of sheer black stockings, slipping them onto her legs smoothly. "Wouldn't this feel divine against your bare thighs, Nick?" she asked, turning to face me. I watched as she walked closer, her body swaying seductively, and when she reached me, laid a hand on my shoulder. Her eyes sparkled with amusement, a half-smile on her lips as she handed me the stockings.
"Here, give these a try," she urged. "You're going to have to tuck your dick down between your legs though."
Feeling my face grow hot, I looked down at the black nylon covering her hips and thighs. I knew she was right, but the idea of stuffing my incredibly hard cock uncomfortably down into her panties made me groan. Trying not to think about it, I carefully slipped into the stockings as she guided me, standing somewhat awkwardly with my legs spread apart as I tediously rolled them up my thighs.
"There you go, bro," she uttered affectionately, a teasing grin tugging at her lips as she tugged at the sides of my dress to ensure the stockings were being held up properly.
I couldn't help but feel the heat rising to my cheeks as I stared down at my bulging fabricated curves, my mind swimming with a strange blend of mortification and exhilaration.
"So, just don't cum, that's all I ask right now," Stacy quipped softly, her eyes twinkling jovially. "But I must say, big brother, you look rather 'femme' in that get-up."
I looked at my sister, my face burning hot, and just smiled nervously. I wasn't sure if I could go through with this, especially with the way my cock was already straining against the satin panties and nylon stockings. I swallowed hard, feeling a lump rise in my throat.
"I... I don't know, Stacy," I stammered nervously. "I've never done anything like this before. I don't even know if I can do it. I've only ever worn lingerie before, and only in private. This is taking it to a whole new level." I mumbled to myself, staring down at my bulging crotch encased in the silky panties. The fabric was clinging to my manhood, leaving me in a state of slight discomfort.
I cautiously adjusted my position, trying to make the straining fabric caress my stiff cock more comfortably. However, the fit was snug, with barely any room for flexibility. The fabric was smooth, and each movement I made began to drive me insane with the stimulation on my sensitive manhood.
Stacy, seeming to notice my discomfort, reached down and gently adjusted the panties, tucking my straining erection between my thighs in a way that was far less uncomfortable.