Sister's Clothing Trap

Editor's note: this story contains scenes of incest or incest content.

*****

Synopsis:

A young man discovers new and confusing things about himself while trying on his older sisters clothes.

And, unfortunately, while he's discovering his sexuality, his sister discovers him.

(This is a one-shot I've been working on while finishing up my other story. The last chapter is coming, don't worry! It's just...taking a lot longer than I thought).

Everyone in this story is 18 years of age or over.

***

I was so focused on organizing my Magic the Gathering cards in the living room that I didn't hear the sounds of high-heeled feet approaching until my step-sister was directly in front of me. It was a Friday night and I'd assumed I was home alone, so when I looked up to see her standing there I yelped and dropped the cards I was holding.

'What the hell, Riley!' I clutched at my chest and glared up at her. She was dressed in a figure-hugging black dress and had her blonde hair neatly brushed to the side. 'Don't sneak up on me like that.'

She burst out laughing and dropped next to me, ruffling my hair with her slender fingers as she did so. 'Dude, I'm in heels. You should have heard me coming from the other side of the house.'

I blushed at her touch and ran my eyes over her before quickly focusing back on my cards. Riley was beautiful, tall and elegant with a body most models would kill for. She had a near-perfect hourglass figure complete with long legs, large breasts and a cute butt. Her face was gorgeous too, round and well-defined with plump, glossy lips and large green eyes.

'I didn't hear you,' I muttered, picking up the dropped cards, 'I was too focused on organizing these.'

She frowned at the meticulously organized collection of cards and plastic sheets in front of me. 'Still? I thought you did this yesterday.'

'I did, but just my black ones,' I showed her cards in my hands, with a finger pointing to the blue circle under the fantasy artwork, 'these are my blue ones.'

'Hmm,' she inspected one with her pink manicured fingers and sighed, 'I don't know why you collect these when you don't even play the game.'

'Because they look nice, especially when they're organized properly,' I patted the large black binder I was currently filling and grinned, 'when I'm finished this is going to look amazing! Do you want to see it when I'm done?'

'Uh...maybe,' she gave a noncommittal shrug and her lips twitched, 'looks like you've got a fun night ahead of you.'

I think she was being sarcastic but I really was going to enjoy myself so I beamed at her. 'Yep! It's going to be great. What are you doing?'

'I'm going to a party with the girls,' she got up and gestured at herself, 'how do I look? I bought this dress just for tonight.'

I took in her whole appearance and felt my heart skip a beat. Riley had somehow made a career out of looking sexy while partying and uploading pictures of herself to the Internet, so she typically looked flawless and today was no exception. Her dress was made out of a silky material that perfectly hugged the curves of her body and its plunging neckline gave a fantastic view of her cleavage. A silver choker circled her neck while matching bracelets adorned her wrists, with a pair of black high-heels finished off the look.

'You look good. Really pretty,' I said as steadily as I could, hoping my voice wouldn't give away how attractive I found her.

'Aww, thankyou,' she clapped her hands together with a smile, 'you're a sweetie.'

I grinned stupidly and wiggled slightly on the couch. Being complimented by her always made me feel amazing. She was so pretty! I was so lucky to be living with her.

'You know, speaking of clothes,' her smile took on a teasing edge, 'I was cleaning out my room yesterday and found a few that don't fit anymore, so I put them in a bag to donate to charity. But, I was thinking...'

As she trailed off my grin froze and panic jolted through me. Why'd she trail off like that? What was she thinking?

...did she know what I'd done last week?

I tried to calm down and nonchalantly met her eyes. 'Oh? Thinking what?'

'That maybe they'd fit you!' She beamed and my stomach did painful back-flips. 'Did you want to try them on? There's a really cute top and some thigh-high socks that'd look great on your legs.'

Oh god. Why was she asking me about wearing her clothes now? Did she know? I couldn't think of any other reason why she'd be asking me about this now. Crap!

Last week I'd...gone into her room. Not for perverted reasons though! I'd just been curious about how her clothes would look on me. I was slender and petite, with a round, doll-like face that had long eyelashes, pouty lips and silky black hair that I kept long. Unless I told someone I was a boy they assumed I was a girl, even when I was in obviously male clothing like my school uniform, so as I'd grown older I'd started to wonder...if I looked cute even in boy's clothes then how would I look dressed as a girl? Would I be even cuter? Maybe beautiful? Or even...sexy? I needed to find out!

Unfortunately, for most of my life there hadn't been a way for me to find out. Mum left when I was a baby, I was an only child and went to an all-boys school. I had no avenue to explore my desires and over the years they fell to the wayside, with my attention turning to video games and Magic the Gathering. I was good at drawing though, so much so that I was planning on making a career out of it after college, and I often drew pretty girls in cute clothes. It helped take the edge of my desires but never fully removed them.

Things changed though when dad married Riley's mum, resulting in all of us moving in together. Mine and Riley's rooms were across from each other and she always left her door wide open. Every morning I'd come out and see her room overflowing with cute clothes and my desire to see myself dressed as a girl returned with a vengeance.

But...I wasn't exactly proud of how I felt so I'd tried to resist. Dad had a very narrow view on gender roles and raised me to be a proper man, someone who would find the idea of wearing women's clothes disgusting. He barely tolerated me having long hair so if he caught me wearing girl's clothes there was no doubt in my mind that he'd disown me, and as someone who'd just turned eighteen and had no life skills that wouldn't end well for me. I couldn't draw my way out of homelessness.

So I'd resisted for as long as I could, but last week I'd succumbed. Friday was date night for our parents and Riley spent most nights out partying so I'd had the house to myself. After months of resisting I just couldn't control myself any longer and crept into Riley's room, practically drowning in excitement. Surely just trying on her clothes just once couldn't hurt? Nobody would ever know!

Things hadn't gone as planned, as it turned out Riley's clothes were too big for me. She was taller and wider than me in every regard so almost nothing fit, and the things that did made me look stupid, like a child dressing in their mothers clothes. It'd been incredibly frustrating and more than a little embarrassing. Riley was twenty-one and in perfect shape. As a man I should have been bigger than her, not smaller. Urgh.

With a heavy heart I'd slunk back to my room and returned to the comforting world of Magic cards and drawing. I was positive I'd put the clothes back in the right place but, well, I'd tried on a lot of things and didn't have the greatest memory. It was possible something had been put in the wrong place but Riley hadn't mentioned anything the next day so I'd hoped I was in the clear.

And maybe I still was? If she knew I'd worn her clothes then she'd confront me directly about it, not attempt to bring it up in a side-ways manner a week later. She was probably just suspicious and this conversation was an attempt to

trap me, to make me admit I'd worn her clothes. Well, I wasn't going to fall for it!

I crossed my arms and met her emerald eyes, hoping that my prolonged silence hadn't made her suspicious.

'I don't want to wear your clothes,' I said in what I hoped was a disgusted tone, 'that's weird.'

'Aww, don't be like that. You'd look really cute in them,' she pouted but I gave a firm shake of the head.

'No.'

'Alex...come on. Do it for me?' She placed her hands on her heart and smiled. 'I've always wanted to see what you'd look like dressed as a girl. I think you'd look really cute.'

Her words made me blush and for a moment I started to give in, wondering if she was being sincere. Wouldn't it be amazing if she was? I could be like her little sister! She could help me so much, like with make-up and buying clothes and stuff. It'd be wonderful.

Hopeful warmth began to coalesce in my stomach but I quickly stamped on it. No! I couldn't risk it. If Riley was trying to trap me then I'd be walking right into it and the consequences would be far too severe. She'd definitely tell dad that I'd been wearing her clothes and that'd be the end of everything.

'N-no!' I shook my head again. 'I'm not going to wear your clothes. Stop asking.'

She grimaced and looked at me in silence for a moment before letting out a heavy sigh. 'Fine then, be that way. If you change your mind the clothes are in a pink bag on my bed.'

'I'm not going to change my mind,' I muttered, although I felt my cheeks warm. If there really was a bag of cute clothes in her room that fit me then there was no way I wasn't going to try them on.

I'd just be more careful this time.

'Alright then,' she gave a half-shrug and brushed a loose strand of hair from her eyes, 'I'm going to head off then before it gets too late. Enjoy your cards, sweetie.'

'Thanks. Enjoy your party,' I waved at her and gave what I hoped was an innocent smile.

'I will,' she returned my wave with a nod, 'seeya later.'

I waited a full minute after she left before jumping to my feet, excitement thrumming through me in warm waves. Any shame or reservations I felt about wearing girls clothes were drowned out by the sudden opportunity to finally realize my desires. This was potentially the last chance I'd have to wear girls clothes for years, as I didn't have any plans on leaving home after graduating, so I needed to seize this moment before it disappeared forever.

As I padded down the hall to Riley's room I became fully swept up in my excitement. It was a odd feeling, wanting to dress as a girl. It wasn't arousal and it wasn't like hunger. It was more of a need, a squishy feeling that first appeared in my stomach like a whirlwind of butterflies, and then stretched out to my chest and head, filling me with a pulsing desire that got stronger the closer I came to wearing girls clothes. It almost made me feel like I was floating, as a tingling feeling encased my body and seemed to detach me from reality a bit, as if I were a ghost.

Riley's bedroom was large, fragrant and extremely feminine. Her fruity perfume permeated the air and, combined with the pastel pinkness of her furniture, gave the room an unmistakable air of femininity. Discarded clothes littered the floor and bed, ranging from dresses and stockings to lingerie, and her large vanity was a mess of make-up and jewelery. She'd adorned the walls with posters of female vocalist and her walk-in wardrobe was fully open, showing off a ridiculous amount of clothes. The bag she'd mentioned was in the middle of her bed and I upended its contents in a rush. A black tank-top fell out, along with a pair of white panties and bra. Thigh-high white socks accompanied them and finally a pink plaid skirt.

A shaky breath escaped me as I held each one up for inspection. Were these really Riley's old clothes? They weren't her usual style at all. She favored more elegant, sexual clothes and these were more on the cute side. I guess she bought them to try out a new style and ended up not liking it.

I picked up the panties and blushed. They were made out of fine silk and had a cute black bow near the middle. Would it be weird for me to wear these? I hadn't even looked at Riley's last time I was here, nor her bras, as that felt way too invasive and pervy. But she'd said I could wear the clothes in the bag, and these were in the bag. They were so silky and soft! I wanted to feel them on my skin so badly.

And the thigh-high socks too. And the skirt! And the bra! I...couldn't not wear any of these. Wah!

I clutched my chest to calm my heart and then organized the clothes in the order I was going to wear them. Bra and panties first, then the skirt, then the top and finally her socks. That was the normal order, right?

After that was done I quickly undressed. It felt weird getting naked in Riley's room, just like it had last time, but I had no choice. I didn't have a mirror in my room and there was no point in trying on the clothes if I couldn't see myself. Besides, it wasn't like my body was very masculine. I'd shaved my body-hair and face before coming here last time and none of it had grown back. I adored the feel of my smooth legs, how my hands glided up and down them, and how they felt in pants. I had wider hips that normal for a boy and a slight waist, complete with slender shoulders and a long neck. If it wasn't for my genitals (which I'd shaved as well) then I'd probably pass as a girl. So while I felt weird being naked in here, for better or worse I didn't exactly look out of place.

Once I was naked I took a deep breath and slipped on the panties, my stomach tensing in excitement. To my extreme delight they fit and, more than that, they felt amazing! They were comfortably snug, the white inlay caressing my butt and genitals in a way I'd never experienced before. My genitals weren't very large and I was easily able to squish them back so they only made the smallest of bulges.

I sat down and looked at my reflection in the wardrobe's mirrored doors, awed to see that I really did look like a girl in the panties. The feel of the silk against my skin was so smooth and tight, delightful in such a foreign way, and a shiver crawled down my back. I rubbed my legs together and giggled, then to my surprise felt a spark of arousal shoot through my stomach.

Eh! What was that? I didn't want to get turned on by this! I was just...getting confused. Seeing a girl in panties was always hot, even if that girl was me.

I rubbed my legs together again and wriggled on the bed, for a moment just enjoying the new sensations, then grabbed the white bra. It matched the panties, being made out of the same material with a matching black bow between the cups. It fit just as well too. I had to put it on backwards to use the clips but once I slipped it around and put my hands through the straps it hugged my skin like a snuggly kitten. The cups were tiny though, nearly completely flat against my chest, and I frowned at that. There was no way these would fit Riley and she'd have been able to tell just by looking at them. Why'd she even buy them?

I probably should have thought about that more but once again the new sensations consumed my mind. My nipples were sensitive and having the soft cups rub against them felt amazing, especially when I pushed hard against them. And just the foreign feel of it all on my body, half-way up my back and chest, was exciting somehow. It looked good on me too, along with the panties. My reflection showed a pale, thin girl in her underwear and I felt another flush of arousal. I looked better than I'd ever dared hope, and for some reason that was really turning me on. I posed a few times in front of the mirror, using poses I'd seen Riley take in photos as a reference, and let out a joyful squeal at how girly I looked. I-I loved this!

I needed more!

I grabbed the tank-top and threw it on. It had a frilly hem, small v-neck and was made from a soft cotton that felt great against my skin. It fit just as well as the underwear did, like it was tailor-made to my body. I admired myself for a moment, liking how the black stood out against my pale sin, then turned my attention to the pink plaid skirt. I'd wanted to wear a skirt ever since I'd first seen girls on TV wearing them and my hands trembled slightly as I slipped it up my legs. The hem ended a half-way down my thighs and angled out at the sides, accentuating my hips and butt. Butterflies stormed through my stomach as I stared at myself and made a few poses, then ran my hands over the skirt. It was so light and soft, and I could feel my body's warmth through it. It went great with the top and I wiggled with joy at my reflection, at how cute I looked. How nice I felt, how comfortable and...happy...

After a while I dropped onto the bed and stared at my reflection with a stupid grin, which grew wider and wider until a stream of delighted laughter escaped me, fading into giggles as I struggled to control myself. Oh my god! This was amazing! I...I couldn't even put into words how good I felt. Euphoric? I was so happy I felt drunk despite not having had a drink in months. This was everything I'd hoped for and more. These clothes were perfect! I didn't look like a boy wearing girls clothes, I looked like a girl. Just...just like I'd always wanted. The arousal from before had faded to a small pulse in my stomach, overwhelmed by the pure joy I was experiencing.

Myriad pleasant feelings surged through me as I stared at myself, but after a while some unpleasant thoughts began to creep in. I...really liked looking like a girl, and that could mean a lot of things, one of which was the possibility that I was trans. I was pretty sure I didn't WANT to be a girl and was just curious about looking like one, but it wasn't something I'd allowed myself to think about much. There was no way dad would let me transition so there was no point in even considering it. I had no future as a transgirl.

But, how happy I felt right now was impossible to ignore. Did this mean I was trans? That I did want to be a girl? How was I supposed to know that? Did I not like being a boy?

I took a deep breath and slowly let it out, then stomped on the confusing thoughts cluttering my head. I didn't want to think about them, especially when I was so happy. They were souring my mood and right now that was the last thing I wanted. I let out another breath and stared at my lap, enjoying how nice the skirt felt and how feminine my thighs looked in it. I-oh! The socks! I'd completely forgotten about them.

I picked them up and inspected them for a moment, wondering how best to put them on. They were made from a soft, thin cotton that didn't have any lines or designs on it. Just pure white. After carefully rolling them up, I slipped my legs through each one in a pleasantly fluid motion and found that they ended just before the hem of the skirt. A sliver of thigh showed and for some reason it seemed lewd, even moreso than if my legs were bare.

Arousal throbbed inside my stomach and I blushed, swinging my feet to and fro. Then I got back to my feet and drunk in my appearance, intoxicated by how cute I looked. I bounced from foot to foot and then started posing again, making peace signs and sticking my butt out, this time using images I'd seen of various anime girls as a reference. I wa-

'Well. You look like you're having fun.'

I screamed and spun around to see Riley staring at me from the doorway, a delighted grin lighting up her face. Holy shit what the fuck?! Oh god!

'Riley?' I croaked and just stared at her with huge eyes, too horrified to even move.

'Sorry to surprise you,' she breathed, entering the room and closing the door behind her, 'but I knew you wouldn't be able to resist trying on those clothes.'

My mind scrambled to process that but I was too panicked to make sense of it. 'I-I-I'm sorry! I'll get changed, I-'

'No! Don't change,' she grabbed my shoulders as I rushed to grab my clothes and looked down at me with shining eyes, 'let me get a good look at you.'