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An Intense Desire To Dress Gurly

"A sissy story of self discovery."

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Author's Notes

"A sixteen-year-old boy discovers his older sister's and mother's lingerie..."

Stepping out the bathtub, I grabbed a soft towel and slowly dabbed the water from my slender smooth legs. I could feel the surge of hormones rampaging through my mind and body as I touched my soft skin.

In the corner of the bathroom was a laundry hamper that was stuffed with various female garments that belonged to my sister. I remember noticing the strap from a silky pink brassiere that dangled from the edge of the hamper as I stood there naked, dripping on the bathroom rug.

My inquisitive mind raced and my hand curiously reached for the garment, feeling the soft sensation of the silk material as it wrapped around my fingers.

Instinctively, I put my arms through the straps, feeling a tingle as the silky material stretched around my rib cage. I reached back, struggling to connect the clasps behind my back, feeling a small sense of achievement when they finally clipped together.

I rummaged through the hamper in search of more clothing, finding a pair of purple frilly panties. I lifted my legs one by one, stepping into the panties and slowly pulling them up my thighs and over my plump bum. The silky material sent electricity through me as it brushed against my soft skin, encouraging me to rub my tiny penis over the panties.

'Why does this feel so good?' I thought, reaching inside the hamper to see what else I could find. After rifling through several more items of clothing, I discovered my sister's short pleated gym skirt, frantically rushing to wrap it around my tiny waist, shaking with adrenaline as I buttoned the side.

'Oh my god,' I thought, 'this feels so fucking hot.'

Something was happening to me, it wasn't just my outward appearance that was changing, my mental state was transforming and I was starting to feel so feminine, gentle and delicate. Inside my mind, I could hear a soft faint voice speak, "you're such a pretty girl, look how feminine you look!"

Unable to control myself any longer, I dropped to my knees, quickly reaching under the pleated skirt and pulling out my tiny hard cock from the silk panties. With one hand I jerked my cock desperately, using the other to rub the silky brassiere as spunk began shooting wildly across the bathroom floor.

Stream after stream of hot sticky come squirted out of my penis, leaving a sticky mess on the bathroom rug and stains all over the pleated skirt. As the last few drops oozed out of my tiny penis I snapped back to my senses, instantly feeling shame and regret at what I had done.

I rushed to strip off the garments, trying desperately to clean up the mess and not leave any evidence of my guilty deed. 'What kind of a sick boy wears his sister's clothes and masturbates in them?' I thought.

Waves of embarrassment ran through my mind as I stuffed the last few items back into the hamper, ensuring to leave the bra strap dangling in the same place that I found it.

Weeks went by and I could barely even remember the experience, assuring myself that it was a one-time thing that likely every guy had tried at least once in their lives, until the next time I was left alone in the house again.

My mom and sister were both out and wouldn't be back all day. I remember watching an old movie that contained a scene with a woman who wore a tight fitted mini dress. The camera panned up from her high heels, slowly and seductively moving up over her stocking-clad legs, past the hem of her dress and up towards her large luscious cleavage.

The lady was very sexy, but I remember it wasn't the girl who turned me on, it was what she was wearing! I jumped off the couch and almost tripped as I ran into my mom's room, racing to search through all her drawers in hope of finding some appropriate lingerie to wear.

I had the urge to dress completely girly from head to toe and knew she had some sexy feminine lingerie tucked away. In one drawer, I stumbled upon a pair of silk lace vintage high-waisted knickers that pressed tightly against me, concealing my tiny penis nicely as I put them on.

In the same drawer, I found a delicate silk and lace trimmed brassiere that perfectly matched the style of the panties and made me blush as I clipped it on behind my back.

As I stood there trembling with excitement, I searched the drawers for something else, smiling to myself as I pulled out a pair of smooth ultra-sheer black pantyhose. I rolled them up onto my fingers and slid them over my toes as the material stretched tightly against my legs.

I ran my hands up over each leg slowly, feeling the soft sensuous feeling of the sheer stockings rub against my skin, finally stretching them over my ass and onto my tiny waist.

'Now I felt like a girl,' I thought, starting to think and act effeminate. My body felt delicate and light as I glided across the hall and into my sister's room, enjoying the sensation of the silk against my skin.

Hunting for something to wear over my lingerie, I rummaged through her dresser, eagerly in search of some sexy clothes. I wanted to wear something that would play to my figure and accentuate my curves.

My sister owned quite a few dresses, but I most desired one that would create a feminine look, taking advantage of my slim frame, long legs and curvy ass to create an hourglass silhouette.

In no time at all, I found what I was looking for. It was a symbol of elegance. A lustrous, satin fabric party dress that glimmered in the light, reflecting the sun from the window. As I stepped into the dress, sliding it over my body and up over my shoulders, I noticed how beautifully feminine I looked.

The dress fit flawlessly and moulded to my slender body beautifully, complimenting my shape. The dress draped over my waist, slightly drifting from my hips and hugging my legs as I moved. The strapless neckline revealed my precious collarbones and gentle, soft shoulders, making me adjust my posture, pushing my shoulders back and poking out my chest and ass.

I wanted to practice my feminine poise, adapting my demeanour to appear more feminine. Every movement became girly, more effeminate while I practised sitting, standing, kneeling, walking and talking like a girl.

I asked myself, “Don't you look like a girly girl? Yes, you do, don't you! Such a naughty little girl,” I said, giggling to myself as I pranced in front of a full-length mirror.

My breath drew shorter, overwhelming me as I took deep gulps of air, completely overexcited by the entire experience of becoming a girl, both mentally and physically. Letting go emotionally and drifting away into the mind of a beautiful, prissy, sexual girl.

'I could do anything,' I thought, thinking of all the possibilities. 'Anything would feel good if I was dressed like this, " I thought.

I lay on the bed, relishing in my new attire. My tiny stiff penis rubbed hard against the soft silk knickers, just aching to be played with. I rolled onto my stomach, reaching out for the headrest and gripping the metal bed poles. I imagined the motion of two people fucking making me gently start to push my weight against the mattress.

The bed frame squeaked like a tiny mouse, trying desperately not to get caught. My heart continued to pound and thud inside my chest. Nothing mattered anymore. Nothing existed outside this room, outside this moment.

'Wow! What was that!' I screamed inside my head, as a warm, wet sensation emanated from my pelvis and started flowing out across my stomach. My whole body shook and convulsed uncontrollably, as the hot feeling came from the center of the bed and filled me with orgasmic vibrations.

After several more involuntary shakes and grunts, I tried to move, struggling to lift my slender arms. I arched back and looked down at the soaking wet bed, realizing what had just happened.

'Oh no!' I thought. 'No one could know! How was I going to do to hide this?'

The dress now clung to me, drenched in come. I tried to peel it off but it slipped through my fingers and snapped back hard against my skin.

'Please,' I thought. 'No one can find me like this!'

I ran in panic, my eyes watering in fear as I rushed into the bathroom, tearing off my clothes and stuffing them into the sink. I began desperately scrubbing the stains from the delicate silky knickers, the sheer pantyhose and my sister's satin fabric dress. Taking each washed item and quickly hanging them to dry over the tub.

'They'll be home soon!' I said to myself. 'Then they'll start asking you why there's wet lingerie in the sink.'

My sister and mom's voice whined and echoes inside my head in a high pitched overtone.

"Why is my bed all wet and sticky?"

"What happened to your sister's pretty party dress?"

I had never experienced anything like it before, a pure euphoria followed by the kind of fear that sent shots of adrenaline through my veins. After several more frantic minutes, I cleaned up the evidence. I even managed to throw on a t-shirt and a pair of jeans, reverting back to my normal self again.

My sister came home first, closely followed by my mom. Neither of them noticed anything when they returned and nothing was said during dinner. After we finished eating we sat and talked for a while until suddenly I realized... I was still wearing the brassiere!

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Quickly, I made an excuse to leave the table and covertly dashed into my mom's bedroom to return the bra back to its original place. Quietly sneaking out and back into my room, my heart pumping with excitement.

Months went by and I'd resisted the temptation to dress in any woman's clothing. I had convinced myself that it was just an experiment. Something all boys did out of curiosity. I wasn't weird, it wasn't 'gay'. The words that my friends would have used to describe me if they saw what I had dressed like.

Spring was over and I'd started working in a clothing store for the Summer, which in hindsight was probably the worst place I could have spent my time. I worked in the stockroom and spent most days checking inventory, moving boxes around and occasionally taking items out onto the shop floor.

I worked with a girl called Francesca who always made an effort to look attractive, wearing provocative outfits and carefully styled make-up and hair. I was in complete envy of her femininity and contagious sex appeal.

One day, out of the blue, I found my mind wandering as I stacked some boxes, accidentally knocking over a shoebox onto the floor. The lid popped off and a pair of size 8 women's ankle strap platform pumps fell out of the box onto the floor.

My eyes widened, transfixed on the high heels, the reflective shiny black fabric and the sensuous shape around the toes. My head darted around the stockroom, quickly checking to see if I was alone before grabbing both pairs of shoes, frantically stuffing them down the front of my baggy trouser pants.

I raced to the staff room, jamming them into my backpack, making sure no one caught me in the act. For the rest of the day, my heart pumped hard inside my chest at the thought of being caught with a stolen pair of women's shoes in my bag.

What would I say if someone found them? What excuse could I possibly give to explain why I had them? I didn't relax until I finally got home, back safe inside my bedroom. The rain was pouring outside and no one else was in the house.

I sat staring out the window, creating naughty images in my mind of sexy girls dressed in slutty outfits, jealous of the women who got to wear them every day. My mom always had a few clothing catalogues left laying around the house and I couldn't help myself from picking one up and flicking through the pages.

The first few pages contained a range of modest clothing, some pantsuits and a few styles of conservative skirts, followed by a collection of long floral patterned Summer dresses. I continued flicking through the catalogue admiring the different outfits, the subtle nuances between sexy and casual wear.

The various lengths, styles, and fits, creating wild images of myself dressed like the women in the pictures. I grabbed the shoes out of my bag, I thought about what else I could wear with them. I didn't want to just dress in a few random items and jerk my cock again. I wanted to look beautiful. To transform completely, to become fully en femme.

I knew the heels wouldn't be enough to look convincingly female, I needed more items to become a 'real girl'. A checklist began to form in my head of everything else I would need to transform. Some pretty lingerie, pantyhose, a dress, a padded bra, a ladies wig and some makeup. I began searching the house, rummaging through wardrobes and cupboards to see what I could find.

My mom had a lot of items on the list, especially in the lingerie department, and I also found a glamourous wig tucked away in a box that she must have worn to a fancy dress party at some point. My sister, on the other hand, owned a lot of dresses that were much more daring, including a few that my mom didn't approve of.

Before long, I had everything I needed all laid out on my bed, quickly stripping down naked and locking my door for safety. First, I slipped on a pair of silk pink panties, then I rolled the pantyhose over my hand, the same way I had seen my sister and mom do when they were getting ready in the morning.

The soft nylon fabric stretched over my toes and up my legs causing a thrilling sensation. As I rolled them up each leg and over my waist, I noticed how sexy I was starting to feel, rubbing my silky smooth legs. Next, I slid my arms through the padded bra, clipping it together at the back and adjusting the cups over my chest.

I looked back down at the bed joyously as I picked up a tiny little satin party dress with criss-cross straps, stepping into it and slowly pulling it up over my legs. The dress stretched tightly as I pulled it over my bum, sliding my arms through the straps and wiggling to find my shape.

'How pretty,' I thought as I donned the wig, making myself look even more feminine and girly, before reaching down under the bed for my bag and opening the zipper. I took the new shoes out and stepped into the platform heels one foot at a time, fastening the straps over my ankles. I'd never worn high heels before, but after a few strides around the room, I seemed to get used to them pretty quickly.

I'd borrowed some makeup and a mirror from my sister and tried my best to apply some foundation to my cheeks, a little eyeliner and of course, some bright red lipstick. My makeup skills definitely required improvement but it felt amazing applying it and made me look dirty and slutty, which gave me a little thrill.

For the next half an hour or so, I pranced around my bedroom, acting girly and appreciating my new persona. I strutted around pretending to be a girl, copying their mannerisms and body movements, transforming slowly, bit by bit. The experience had overtaken me and I found myself role-playing, imaging I was with another person.

My new persona brought out a sexual urge inside me and before long I found myself rolling around on my bed, feeling the nylon pantyhose rub against the sheets. I started dry humping the bed, feeling the soft and silky fabric against my skin, causing me to get an erection inside my silk panties.

Images of Francesca's sexy body flashed inside my mind. 'Yes', I thought, 'you look just like her, you sexy girl'. "Fuck me", I whimpered, "fuck me like a slut."

Abruptly and without warning, I let out a soft moan as my cock began to explode. My whole body started to convulse and shake uncontrollably as each stream shot out of my cock, filling the silk panties with hot sticky come. After several minutes of intense spasms, I finally stopped coming, feeling the sudden shock of reality return.

'What are you doing!' A voice screamed inside my head. 'Not again! Look at what you did!'

I looked down, my sister's dress was completely stained with my ejaculation and so was everything else. "Fuck," I blurted out, quickly stripping down and running to the bathroom. Luckily, I still had enough time before they would be back to try and clean up my mess and remove my makeup. After several panicked minutes, I'd managed to cover up my tracks.

Later, when they did return home, I starting feeling really guilty and ashamed for what I had done. Like a drunken slut with a hangover swearing to never drink again. I vowed I would purge these feelings out of my system and never dress like a girl ever again. I took the shoes and tossed them into my bag, leaving the house and tossing them away into a dumpster.

For the next few months, I kept true to my vows. I had stopped wearing women's clothes and had even started dating Francesca from work. Everything was going well and I felt normal again, even more confident. I was like other boys, manly and full of testosterone.

Right up until the fateful day that I spent the night at Francesca's apartment. The evening had been fairly standard. We ate together, watched a movie and had sex, then fell asleep in each other's arms.

It wasn't until the next morning that things took a dramatic turn. Francesca woke up early and was getting ready for work. I had the day off and was still laying in bed dozing as she walked over, kissing me on the head and telling me to rest.

As the door clicked closed, the sudden realization hit me. 'I was alone in her apartment!'

An involuntary motion took over, forcing me to leap out of the bed and strip off naked. I rushed over to her dresser, pulling open the drawer and frantically searching through her lingerie. Within minutes I was standing in front of her mirror, dressed in a seductive black lace corset with padded cups, wet look trim and sheer nylon stockings.

"Oh fuck, yes baby girl!" I muttered to myself, dropping to my knees and jerking my rock hard cock, moaning girlishly as I brought myself off to an intense orgasm.

As the come splurged out onto my legs, I looked up at myself in the mirror, noticing how slutty I looked and realizing the honest truth. I was never meant to be with girls. I was destined to become one!

Published 
Written by MirandaGreen
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