Crossdressing Charlie Vol. 1: Episode 1 - The School Uniform

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SUMMARY: Charlie is an ordinary teenage boy with a secret wish to dress up in his twin sister's school uniform. Now he is blessed with a rare day at home to himself, allowing him to bask in his deepest desires for the very first time. It is this occassion that kicks off a craze that develops into something so much more as the pleasurable sensations of female clothing takes him into its warm embrace.

The thump of the car door made Charlie open his eyes. The sound of a second door slamming made him sit upright in the bed like a startled squirrel. He listened carefully. The ignition jerked several times before the engine started up. He was still as a statue as he listened to the low rumble of the car reversing out of the driveway. He scurried across the blankets, jumped off the side of the bed and stumbled over a pile of books on the floor towards the window. He parted the curtains and looked down to see his mother’s hatchback van driving away down the street.

His heart skipped a beat, then, a smile slowly spread across his face as sudden realisation dawned upon him. His mother, Mary and his sister, Rachel were gone into town for the day. He was home alone for the entire day and he knew that he could do anything he wanted. He closed the curtains and turned, looking around at his messy room as he scratched his hair heavy head, thinking of possibly inviting his friends over. He could eat and watch television all he wanted. He could spend the entire day in town without his mother wondering where he was.

Yet, he did not wish to do any of these ‘’normal’’ activities. He knew what he wanted. Something he had desired to do for a long time. Something he wanted more than anything but he was never given a chance to do so.

He ruffled his brown hair as he walked towards the door, dressed in only a t-shirt and boxer shorts. He waddled down the stairs, feeling as if butterflies were fluttering about in his stomach. He sat at the kitchen table, munching on a bowl of cereal with his eye constantly on the clock. It was 08:57.a.m.

As soon as he finished breakfast, he grabbed two oranges from the fruit basket and ran upstairs. He went to the bathroom, urinated, and brushed his teeth. He stripped down naked and hopped in the warm, steamy shower. He let the water pour down over his long, shaggy hair as the shampoo cleansed it softly. He scrubbed himself down from head to toe until he looked and felt spotless.

He got out of the shower, wrapped a towel around his waist and tip toed down the hall to his bedroom, leaving trails of water behind him. His teeth chattered as the cold air got hold of his warm wet body. He closed the bedroom door behind him and began to dry himself. He then walked to his mother’s bedroom, naked and bare to use her hairdryer. Using the hairdryer was the only way he could dry his soaked hair without it curling. He hated it when it curled.

The second he was done, his stomach lurched with excitement. He felt as if he was floating down the hallway, passing his bedroom door, the bathroom and the spare master bedroom until he reached the last door, his sister’s bedroom. He placed his hand on the handle, uncertainty swelling up.

What if I’m caught - but then again how could I? Charlie thought. I’m home alone all day!

He looked down the hall, then slowly pushed the handle down, and gently nudged his sister’s bedroom door open. It creaked. The room was tidy, bright, and well lit. A double bed was placed in the centre of the room, draped in white blankets and sheets with red polka dots. A large wooden wardrobe was placed in the corner, beside the window where a desk was situated, stacked with piles of books and school items. The walls were painted light yellow with posters of boy-bands, teen idols, famous actors along with a lot of puppy and teddy bear pictures. On the right wall to the bed was a makeup station, stocked with tubes of lipstick, eyeliner, eye shadow, nail polish, makeup sets, lip-gloss, boxes of rings, earrings, necklaces, pearls and the likes.

The placed reeked of girliness. It made Charlie feel incredibly out of place and even a little intruding. His sister must never know. He stepped into the room, shutting the door behind him and turning the key, just in case. He took a deep breath as he looked around the room. If he looked like anything at that moment, it would be a little boy, gazing at a never-ending toy store which was open for him to play in for as long as he liked. He looked at the wardrobe coyly, feeling guilty in defying his morals just to bask in a pool of pleasures.

Then, he felt as if somebody nodded and smiled, saying it was okay to let himself free. The larger half told him ‘’he deserved it’’ after the never-ending wait. He pranced across the room, his towel wrapped around his waist as he plunged into the soft cushiony bed. The faint whiff of perfume filled his nose as he breathed in the feminine atmosphere. He closed his eyes and smiled blissfully as if he were on cloud nine.

This is it!

He got up after a few moments, opened the window to let in some fresh air, and walked to the full-length mirror. At the age of sixteen, his average height, skinny frame continued to bother him despite it being currently very beneficial. He then turned to the chest of drawers as his heart pounded against his ribs with excitement. He opened the top drawer, which revealed a wide array of panties, knickers and underpants of all colours and patterns.

He felt that his current actions were so wrong and for a brief moment, he thought about aborting his desires for the day. However, he had come too far; it had to be done now. He knew he would not get another chance for a long time. He reached in and took out a soft cotton pair of knickers with pink polka dots and a bow at the front. He felt his cheeks turn red as a wave of embarrassment spread throughout his body. He felt as if he were standing in a steam room as his breathing became repressed and his skin started to boil.

He felt something tick inside him as he touched the bow on the front. He looked around the room again, just in case somebody happened to be there watching. He let his towel fall, crumbling around his ankles as the light chill of the room caressed his skin. He took a deep breath and smiled to himself as he stepped into the knickers. He pulled them up above his legs, feeling the smooth fabric brush against his hips as he adjusted them around his thighs.

He shivered all over as the hairs stood up on the back of his neck. The feeling was electric. He walked to the bed and picked up the two oranges he had brought up with him. He then opened the second drawer and pulled out the matching bra. It was white with pink polka dots, extra layers of satin padding with lace trimmings around the edge of the cups. He placed the two oranges inside the cups and held the bra up to his chest with great difficulty. The oranges fell out a several times, which quickly made him feel frustrated. It took him a few moments to fasten the buckles together and even longer to tighten it correctly.

The sudden feeling of weight and pressure against his chest made him tingle all over. Goosebumps spread over his arms and legs. The sensation of the straps on his back made him feel oh so feminine. He then took a pair of tights from the drawer. They were white, thin, and barely transparent. He put his legs into the crumpled up garment and stretched it up his shins, over his knees and over his knickers. The soft feeling was immense and it made him feel incredible. He wiggled his toes between the soft fabrics of the tights and stroked his legs smoothly. It was heaven.

He then turned to the wardrobe, his pulse throbbing as his excitement escalated to massive heights. He had always wanted to do this and now it was his chance. Finally. He opened the two doors, which revealed a massive collection of girly outfits owned by his twin. There were skirts, dresses, blouses, leggings, sweaters, cardigans, camisoles, tank tops and shirts hanging inside. There were also slippers, runners, high-heels, boots and formal shoe wear in the foot-drawer.

Charlie’s eyes trailed back and forth, analysing each outfit. Then, he spotted it, hanging there in all its glory. The school uniform. His knees began to tremble as he pulled it out of the wardrobe. He had waited so long for this moment and now it was here. He walked across the room, not taking his eye off the uniform as he touched the fabric of the sweater. He picked the blouse first. It was white; round collared, long sleeved, and had been moulded to fit his sister’s shapely abdomen and bosom. He put his arms in the sleeves, noticing the snugness as he pulled the soft blouse around his bodice.

He looked at the door once more to see if anybody was watching him. There was nobody. He then buttoned up the blouse, one by one and over his false breasts until he reached the second last button. He left the top two open. Slowly but surely he began to feel slightly more feminine which was what he wanted. He exhaled through his nose as he focused on the soft cotton fabric hug his torso, false breasts, and arms tightly.

He looked back at the uniform laid out across the bed. He was more than ready for his favourite part. The skirt. He picked it up and held it In front of his eyes, admiring its girlish delicacy. It was short, high waisted, with a dark navy, blue and thin white striped plaid pattern. It had light pleats around the hemline with a zipper on the back. He could not understand why he fantasised about wearing such a simple piece of clothing but he was about to fulfil his dreams that very minute.

He stepped into the skirt and pulled it up, the polyester fabric gently stroking against his shins as he pulled it over his knees. The skirt slithered against his skin as he pulled it up over his thighs and adjusted it around his waist. He tucked the blouse in, carefully and neatly. He then zipped up the skirt, tightening the band around his waist. The sound of the zipper gave him chills.

He looked down at his legs, the skirt lengthening half way down his thighs. The feeling of the skirt against his hips and the soft satin panties beneath made him jiggle blissfully. He then picked up the tie. He buttoned the collar of the blouse up to the top and fixed the navy and blue striped tie around the collar. It was neatly tied, perfect and prim.

He stepped in front of the mirror, admiring himself from head to toe, posing girlishly with his hand on his hip and curling his toe with his hands behind his back as he stared into his reflection shyly. Yet, he could not help but blush at the sight of himself. He wondered what his friends would think of him right now let alone his mother and sister. He could not even think of their reactions. He felt he would be completely devastated if they found out.

He was not finished yet. He picked up the thin blue v-necked sweater with the school crest embedded on the right breast. He pulled it over his head and down over his bosom, fitting snugly around his abdomen, yet too tightly against his fake orange boobs. Perhaps he made them too big but he did not care because he simply loved the sensation. He fixed the blouse collar around the neckline and folded the stiff cuffs out over the sweater sleeves.

He then walked back to the wardrobe, opened the foot drawer and pulled out the shiny Mary Jane school shoes. He placed it against the sole of his foot. His heart sunk when he realised that they were much too small for him. But no matter, he had the rest of the outfit to enjoy.

He turned and looked at the makeup station. He wondered if he should put on some makeup despite not having a clue how to apply the stuff! He supposed a little lip-gloss would not hurt anyone. He walked across the room and sat down in front of the station mirror, staring into his reflection. The more he looked into himself, the more he seemed to look like his sister. He looked at all the tubes and containers, spotting a small pink tube. He picked it up and looked in the mirror, slowly and carefully pressing the lip gloss to his lips. He rubbed the gloss off several times as he was not satisfied enough. He was careful not to use too much in case his sister noticed soon he perfected it. He looked into the mirror, pouting and doing kissy lips. He laughed to himself as he shifted about in his skirt, rubbing his toes together inside his tights.

He dared himself to apply nail polish. Would she notice? He quickly brushed the thought away as he tried to be cautious. He did not wish to get too carried away. He picked up the hairbrush and began to stroke his shaggy hair, pulling out strings and split ends. He looked into his reflected eyes as he tilted his head and brushed. His insides squirmed with pleasure as a hot sensation engulf his tummy. He brushed his hair until it was as soft and shiny as could be, lengthening all the way down to his shoulders.

‘’You could really do with a haircut, Charlie!’’ he said to his reflection.

He then brushed his hair down each side, parting it in the middle until he had a somewhat feminine doo. He smiled at himself in the mirror, proud of his own handiwork. He wore various feminine expressions as he modelled himself in front of the full-length mirror. He pushed his butt out as far as he could as he knelt down. He felt his false orange breasts with his two hands and squeezed them gently. He swayed his hips as he paced back and forth from the mirror.

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Charlie could not believe it but he resembled his sister even more so than ever. Well, they were twins but now that he was dressed like her, it still came as a shock. He decided to add some extra accessories to his school outfit such as a pair of his sister old clip on earrings and a bracelet. He did not really like these very much so he took them off after a few minutes. He decided to leave the room, feeling a little nervous as he did so. He unlocked the door and shouted ‘’Helloooooo?’’ down the hall.

Nobody replied. There was not a sound to be heard. He stepped out into the long hallway. He stood still and pondered for a moment. What shall he do now? A smile soon spread across his face as he broke into a run down the hall. For the first time he felt his skirt flow up and down as breeze gushed in and around it. He then skidded in his tights along the shiny wooden floorboards and then turned, running to the other end of the hallway again. He could feel his breasts jump up as he ran, his hair flowing back and his skirt flaring from side to side. It was heavenly.

He then skidded against the ground, stopping to catch his breath. He could not help but feel a little silly after doing that but it was worth it. He then went back into his sister’s room, breathing heavily after the run as he turned on the stereo. He felt that he was beginning to feel a little more at ease wearing the uniform. Ironically the song, ‘’Girls Just Wanna Have Fun’’ started to play.

Suddenly, he had a strong desire to jump up on the bed and move to the music. He never usually danced but sure he was home alone. He could do whatever he wanted. He grinned as he climbed up on the bed and began to jump up and down, feeling like a fool but enjoying the freedom of letting himself go and escaping world. He loved the feeling of his skirt flop up and down as he jumped, exposing his polka dotted panties beneath his tights. He jumped to the music, his hair flying everywhere as he laughed gleefully to himself.

Then, he heard somebody call his sisters name. The song had just ended, leaving the room in complete silence. Charlie was so stunned that stumbled off the edge of the bed, landing face down on the ground. He could feel the oranges within the bra cups squash and spew juice all over his chest. He got up and looked around to see that the room empty. Fully alert and alarmed, he randomly grabbed a hairbrush as a weapon but he dropped it as soon as he realised how ridiculous he looked.

‘’Hey Rachel!’’ called the voice again.

It came from outside. It was a boy’s voice. It sounded rather familiar to Charlie. His eyes darted to the open window. The next song on the CD began and blared across room. His heart was literally in his throat as he began to panic. He crawled across the floor, feeling a massive wet patch soak through the bra as the orange juice dripped down and through the blouse. He scurried for the stereo and plugged it out. He lay on the floor, listening carefully for the voice that would call Rachel again.

‘’Rachel, I know that you are in there! I heard the radio and seen you jumping on the bed like a lunatic!’’ the boys chuckled.

‘’Oh god!’’ gasped Charlie, his hand covering his mouth in panic.

‘’Just come to the window babe!’’ called the voice.

Charlie waited on the ground for a few minutes, his hand over his mouth as his eyes watered with terror. The orange juice was gradually soaking through the blouse and sweater. The boy simply would not go away. Then, the doorbell rang from downstairs. Charlie gulped, not knowing what to do as fear got the better of him.

The boy thought he had just seen Rachel jumping on the bed yet she was supposed to be in the city. If he rang her mobile phone and asked her to go to the door, she would speculate WHO was in HER room, dressed in HER clothing and jumping on HER bed.

The door bell rang again. Charlie knew he had to act fast so he got up, ran to the mirror, wiped away the lip-gloss, and ruffled up his soft hair. He then ran down the hall. ‘’I’M COMING!’’ he shouted at the top of his voice. He then ran down the stairs, feeling the orange juice seep into his underwear. He went to the door, thankful that the glass on each side was frosted, and opened it a crack.

The boy at the door was Dave O’Donnell, a stropping young man who was in the same school year as Charlie and Rachel. He never really talked to Dave but he knew that he was in some sort of a romantic relationship with Rachel for some time.

Charlie poked his head out from behind the door, hiding his uniformed body from view.

‘’Hey Charlie, can I speak to Rachel?’’ asked Dave.

‘’Oh sorry she’s not at home at the moment,’’ said Charlie, nodding his head.

Dave’s brow arched. He looked confused and a little suspicious as he attempted to look inside the door.

‘’That’s odd,’’ he said coolly, ‘’because I could have sworn that I seen her up in her bedroom through the window.’’

‘’Oh no that wasn’t Rachel,’’ said Charlie, laughing, ‘’that was my cousin Clara. She came over to keep me company while my mother and sister were out of town.’’

Dave nodded and forced a crooked smile, obviously a little disappointed that Rachel was not home.

‘’Well when she gets back, tell her I called by okay?’’ said Dave.

‘’Yeah sure,’’ nodded Charlie. ‘’Seeya!’’

Charlie shut the door, waited and looked through the letterbox to watch Dave leave. As soon as he was out of sight, Charlie locked the door and gasped in relief. He turned, leaning up against the door with his eyes closed as he slid down on his bottom. ‘’I’m never doing this again!’’ he swore to himself.

He walked to the kitchen in his sisters soaked wet school uniform and tried to enjoy his last few minutes being in his schoolgirl uniform before taking everything off and throwing the outfit into the washing machine. He watched it turn and twist in the dryer, feeling a little sad that he would probably never wear it again.

Then, everything was suddenly back to the way it was except for the fact that he was now standing naked in the kitchen, but normal nonetheless. He took some detergent and a mop upstairs with him to clean the puddle of orange juice from his sister’s bedroom floor. But first he stopped by his cluttered bedroom to put on a pair of underpants, blue jeans, red t-shirt and socks. He felt that male clothes were so bland, bleak and not fun to wear. What was the point?

He sighed mournfully as he entered his sister’s room, mopped up the orange juice and dressed the bed back to the way it was. He even went for the extra detail by turning the track back to the previous one on the CD, moved objects back to their original positions and sprayed the room with a hint of his sisters perfume in case he left any scent. He made sure that there was no way that anybody could find evidence to trace back to him.

After a short while of watching television, Charlie hung the uniform in the back garden on the washing line. He looked around to see if any of the neighbours could see him but there was no sign of life. He hung each item on the line, the blouse, the sweater, the tie, the knickers, the bra, the skirt and even the tights. He was trying to follow the pattern in which his mother washed clothes. The day was warm with a light breeze in the air. Perfect weather for drying.

He sat in the back garden on a deck chair, watching the uniform sway on the line with the wind. He started to think about why he had wanted to wear it so much. It was not anything sexual but he got a different kind of pleasure in girls’ clothing, a pleasure he had never experienced before. He liked it. He felt comfortable, at ease with himself and that slightly worried him.

The fear and thrill of nearly being caught by someone excited him a little. He did not know why but it just did. He wondered when he would get a free house to himself again. He assumed it would not be for a long time but that did not mean he could not look forward to it.

Wait a minute! I have the rest of the day alone. I can try on my sister’s clothes all I want! Charlie thought.

He was just about to get up from the chair when suddenly he remembered what just happened earlier. ‘’No,’’ he whispered to himself, sitting down. ‘’It’s too risky.’’ He sat back down on the chair and continued to enjoy the weather whilst he watched the line. Soon, the uniform was dry and he went inside to get the basket.

He unclipped each of the pegs, letting the skirt, the blouse, sweater, tights, bra and panties fall into the basket. He looked down at them, mesmerised by them. He knew he would miss them. Suddenly, he no longer felt alone. He looked up to see his best friend Sean walk onto the garden with his bicycle.

‘’You swear you never seen a pair of knickers before!’’ said Sean.

‘’Jesus Sean! You nearly gave me a bloody heart attack!’’ said Charlie, feeling his heart pounding.

‘’Alright man, calm down!’’ said Sean cheekily. ‘’No need to get all flustered just because I caught you doin’ the washing like a lady!’’

‘’I’m not — I — my mother is paying me to do the washing today while she’s gone,’’ lied Charlie defensively.

‘’Yeah I do not really care what you get up to in your spare time to be honest,’’ said Sean truthfully. He paused for a moment, looking at the washing basket with a certain glint in his eye. ‘’How do fancy going downtown to meet the lads?’’

Charlie looked up at the window upstairs, then at Sean wondering what he should do. Spend the rest of the day trying on girly clothes or hang out with his friends. He looked down into the basket at the uniform once more and smiled to himself.

‘’Yeah sure, just give me a few minutes. I have to do the ironing first,’’ said Charlie.

‘’Ooooooh, hello!’’ said Sean, mimicking a stereotype homosexual.

‘’Shut up,’’ snapped Charlie, pushing the washing up basket into Sean’s arms. ‘’You can help too!’’

Yes, Charlie had fun that day trying on schoolgirl uniform. The day seemed to be nothing more than a simple once off curiosity. It was a close shave, almost being caught, yes, but little did he know that he had just triggered a new part of his life, a trigger that will release a long hidden side to his being, which will take him down strange and dark roads.

The story begins here!

TO BE CONTINUED
I would love to hear your thoughts and comments!

Want to see what happens next? Move onto Crossdressing Charlie: Episode 2 — High Waisted Skirt for more girlish adventures!
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Comments

The school uniform

Would have given a Kudos but its not working.Good story,brings back good and bad memories.Please write another chapter of this.Thanks

devonmalc

devonmalc

There will be plenty more of

There will be plenty more of Charlie's adventures to come! Thanks for reading!

Lily Florette

let down

ok you had me hooked in the beginning but i didnt like the way you cut it off in the end....it was still a good short story

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Its not the end yet. As i

Its not the end yet. As i have stated their is plenty more yet to come. Its kind of like the end of a TV show you know ''to be continued.''

Lily Florette

good story

a funny little story. I suspect Charlie will be crossdressing again.....

Dorothycolleen, member of Bailey's Angels

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=D

Extravagance's picture

That was a fun adventure. Cross-Dressing boys are so cute! ^_^
I think his best adventure ever; would be to somehow be exposed to something that would render him totally androgen insensitive. That way the nasty testosterone won't poison his body and rob him of his passability. He might even grow REAL boobies! ^_^
Oh, and maybe he can have an adventure and find some nicer, supportive friends? = ) That Sean boy was kinda icky. =P

Great writing, looking forward to more! ^_^
*HuggleSnugglePurr* <3

- - -

BCTS's resident Extravagant Honorable Trans-Cat-MegaTomboy! ;D ...But I do like cuddles from soft but strong arms... ^_^
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Charlie's hopefully just begun

Hope you keep writing Charlies' story. Getting caught might be a blessing in disquise. Is he doing as good a job in cevering himself as he say. The rish of getting caught holds anxious moments.

Kind of wish I had gotten caught by someone who cared. My thanks and compliments to a new athor.

JessieC

Jessica E. Connors

Jessica Connors

Superb story!

I really enjoyed this - the expectation in that slow build up, followed by the exhilaration of the dressing, then getting seen. Great!

It's well written and well constructed.

A bit of advice to Charlie - never pad your bra, or especially someone else's with items like oranges, which smell even if they don't burst, and are an absolute disaster if they do. For an improvised quick and clean boob job, water-filled food/freezer bags are ideal. Fill each one with a measured amount of water at body temperature, then expel all the air and tie them partway up the neck, so there's plenty of flexibility in the bag. They form lovely soft breasts (and the evidence is easily disposed of!).

Maith an cailin

There is no location mentioned for this story but I think it could be somewhere in Ireland ???? The names and especially the colloquialisms are what lead me to think this.
I think the writing is of a very high standard, the story has not developed in a major way yet, not a huge amout of dialogue, but it still holds one completely as the detail, characterization, and descriptive powers are all very strong. To summarise a very accomplished first attempt and a promise of great things to come. Kudos indeed !!

Karen

I was born, raised and I

I was born, raised and I continue to live in Ireland as a proud irishman! I never usually like stating the location as i want the story to have a universal appeal! But yes the location is ultimately based off Ireland! :)

Lily Florette

You and I both. The land of

You and I both. The land of Saints, scholars and sissies obviously lol.

Haha If i may be too foward,

Haha If i may be too foward, you probably want to remain anonymous, but what county are you from? I've never met another Irish TG lover. I dislike the word sissy to be honest because I don't consider myself to be one. Don't let these CD stories fool you, i've never cross-dressed in my life! Haha! I prefer to class my TG oreintation as 'curious facination' with the 'other gender' :P

Lily Florette

Cross dresser Charlie part 1

This was an excellent story Charlie had a close call can't wait to read more

Girls rule