SUMMARY: It has been a few weeks since Charlie first tried on his sister's school uniform. He thought it to be just a once off passing fancy but ever since then the only thing that has been on his mind was when he got the chance to do it again. His desires are beginning to grow into something bigger as he takes the day off school to plunge into his sister's wardrobe.

‘’Oh Charlie, you’re burning up!’’ said Mom.

She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water bottle back under the blankets and placed the thermometer back in his mouth within seconds.

Charlie’s twin sister, Rachel entered the room, dressed in the very same school uniform that Charlie had once tried on just a few weeks ago. She had her school bag thrown over her shoulder and an expression of jealousy on her face.

‘’How are you feeling faker?’’ she asked, leaning up against the door frame with her arms crossed.

‘’I’m not faking Rachel!’’ stated Charlie. ‘’I feel rotten!’’

‘’Don’t you think that you’re getting a little old for faking being sick just to get out of school,’’ said Rachel, pursing her lips.

‘’I’m not lying! Why are you even here? Get the hell out of my room!’’ bellowed Charlie.

‘’Rachel, leave your brother alone,’’ snapped Mom, who had just arrived back with the medicine. ‘’He’s not feeling very well.’’

Rachel stood by the door, rolling her eyes as Mom handed Charlie the glass bottle of clear liquid. He took two swigs of it, the taste burning the inside of his mouth and sliding slowly down his throat.

‘’Thanks Mom,’’ he croaked.

She screwed the cap back on and looked down at her son with concern.

‘’Are you sure you’ll be okay at home by yourself?’’ she asked. ‘’I mean your temperature seems to be through the roof and I don’t want to leave you alone.’’

‘’Mom, I’ll be fine! I’m bloody sixteen years old, I can take care of myself!’’ said Charlie.

She didn’t look very convinced as an expression of worry spread across her face. Her eyes watered as she looked back at Rachel who just shrugged.

‘’Well - okay but call me straight away if you need anything.’’

She looked at her watch, her eyes widening with shock.

‘’Gracious! I’m late for work!’’ she bellowed. ‘’Come on Rachel, we need to get a move on.’’

She then rushed out of the room. Rachel was still leaning against the door frame.

‘’Anyway, I’m going to Kayla’s house straight after school to study so I won’t be home this evening,’’ said Rachel.

‘’Study?’’ said Charlie, his heart leaping and his eyes widening.

‘’Yes Charlie, study, you know that thing you never do?’’

‘’Why should I care what you do anyway?’’ said Charlie.

‘’Uh because I won’t be around to cook you dinner so you’ll have to figure out what to eat for yourself!’’ said Rachel, turning to leave.

‘’Well I wouldn’t be able to eat anyway because I’m practically dying here!’’ bellowed Charlie.

‘’FAKER!’’ echoed Rachel’s voice from the hall.

Charlie’s head fell back into the pillow and her stared up at the ceiling, curling his toes and clenching his fists from beneath the blankets. He felt the low adrenaline kick of excitement. He could barely contain himself. He had been given more time to do the thing he loved to do most in top secrecy, cross-dressing. It had been only three weeks since his very first venture into dressing in his sister’s clothes but it felt more like three years.

He listened carefully, waiting for the usual stutter of the car engine before starting up and reversing out of the driveway. He could hear his mother and sister arguing before hearing the thump of the car doors. Then, they were gone, leaving Charlie alone for the next twelve hours. His mother was usually home at half eight and his sister should be back at around that time also giving him plenty of time to bask in his girlish desires.

He lay there for a few minutes savouring the excitement and anticipation before he could no longer handle it. He threw the blankets off and jumped out of the bed. He stretched as high as he could, feeling his joints and muscles loosen. He ruffled his hair, feeling the considerable amount of growth that had taken place. His mother was trying to get him to cut it but he refused to do so. After all, a lot of guys had long hair in school.

He walked to the bathroom, wearing only his boxers t-shirt. He turned on the water, went for a whizz, stripped down and hopped in the shower. He scrubbed himself hard from head to toe, washing every inch reachable. He washed his hair with care as he was trying to retain a soft shiny glow. When done, he grabbed his bathrobe and put it on. He then dried his hair with his mothers hairdryer followed by eating breakfast downstairs in the kitchen.

The time had come once again.

He went up to his sister’s bedroom. The door was already open, exposing the slightly cluttered room. He didn’t feel as nervous as before but he was certainly cautious. He wasn’t taking any risks like last time when he was nearly caught by Rachel’s friend through the window. He stepped inside, feeling the hairs standing on the back of his neck as he stared at the sacred wardrobe. His skin formed goosebumps as he looked around his sister’s room. He hadn’t been there since he tried on her uniform.

The first thing he did was turn on the light and close the curtains. He then shut the door and looked at the wardrobe. His heart was pounding against his ribs as he approached the doors. He opened it slowly, revealing a treasure trove of girly feminine clothes and outfits ranging from uniforms to party dresses. He already knew what he wanted to try on, something he had only seen his sister wear twice.

His fingers ran through the clothes hanging from the rails as he searched for the one he wanted. He couldn’t find it and for a moment and he began to panic but then he realised that he was looking in the wrong place. He closed the wardrobe and went to the chest of drawers. He opened the top drawer to reveal a wide array of his sister’s underwear.

He felt as if hot water was flowing through his veins. His conscious was torn between right and wrong as he stared into the drawer. He was thinking hard about what he should do. Should he abort and forget about it? But no, that seemed to be impossible. His urges were much too strong and he couldn’t help it. The first time was just curiosity but now it was becoming something of an addiction.

Unbeknownst to him, his cheeks were flaring red and his eyes were watering. He looked over his shoulder to see if anybody was there, just in case. There was nothing, just him, alone. He looked back into the drawer at the panties. He closed his eyes, feeling his heart pounding before sighing and picking up a random pair. He lifted them up and analysed the detail. They were white, soft and thin with lace lining around the legs. On the front was a tiny ribbon bow design which sent chills down his spine. He closed his eyes tight.

The voices of his friends and family echoed at the back of his mind.

‘’Are you some sort of faggot?’’
‘’Eww what do you think you are doing?!’’
‘’Charlie, this is just weird!’’
‘’You sick pervert!’’
‘’Just look at yourself!’’

He suddenly snapped out of it, dropping the panties as if they were diseased. He looked around the room, his eyes watering as if he hadn’t blinked for a while. He felt strange and swallowed his fear and guilt. He picked up the feminine underwear, folded it and placed it back in the top drawer, gasping with relief . . . somewhat.

He then left the room.

He couldn’t do it. He couldn’t go through with it after looking forward to it for so long. Something clicked inside him that restricted him from going any further, something called a conscience. It just felt wrong to be trying on her sister’s underwear and clothes behind her back. It was not only an invasion of privacy but of gender too.

He walked down the stairs, his head hanging low as if he were on the way to the principal’s office for punishment. He let himself fall onto the couch in front of the television inside the sitting room. He flicked through the channels searching for something interesting to watch, desperately trying to forget that he ever went into his sister’s room. He changed the station every few minutes, bored and restless of what he was seeing and thinking. He would spot various outfits on the girls on TV and would immediately fantasise, each time he did he would try to brush away the urges by changing the channel. He sat and watched sports for a while, eventually becoming bored and tired.

He turned the TV off and sat with his face buried in his hands. He could feel the strong urge building up inside him once again. He could feel his heart and pulse beating strong as if he had just ran a mile.

‘’Don’t give in, you can do this!’’ he kept repeating in his head.

He looked at the clock; it was nine in the morning. It would have been a complete waste of a day if he didn’t get what he wanted done. He could study? But he laughed at the prospect. He sat on the couch for what felt like an age, tapping his foot to the rhythm of the clock.

‘’Don’t give in, don’t give in, don’t give in!’’ he whispered over and over.

He looked up at the clock to see that only five minutes had passed. He jumped up and went to the kitchen, poured himself a glass of orange juice and drank. The feeling of the ice cold drink sliding down his throat was a fantastic feeling. He then sat at the kitchen island, picked up his phone and started playing with it.

As he sat in silence for a few moments, the urge to dress was becoming much too strong for him to handle. It built up inside the pit of his stomach like a fiery beast, penetrating his veins, fuelling him with pleasurable thoughts and emotions. He had to do it. He could not waste the chance. Days like these were rare and hard to come by. He had to do it.

As he stared at the clock ticking slowly over to quarter past nine, his feelings of guilt and fear quickly flipped over to apathetic and lust. It had to be done. He stood up, feeling confident and excited, not caring about anything or anyone, not even himself. His motives immediately changed back to the way they were right before he opened the underwear drawer.

He was going to be alone in the house all day. He knew he was going to have so much fun.

From his last cross-dressing experience, Charlie learned a valuable lesson, ‘’don’t use oranges as false breasts!’’ because they burst and stain. Over the last few weeks he had been browsing the web on making his own homemade falsies and he found a very adequate solution.

He opened the cupboard under the sink and took out two plastic freezer bags. He placed them both under the tap and filled them with warm water. After that he brought them upstairs to his sister’s bedroom. He closed the door behind him and looked around the room. It still reeked of Rachel’s girlishness. It made goosebumps form on the skin of his arms and legs. He left the water filled bags on the bed and walked to the chest of drawers.

He took a deep breath before opening the top drawer, once again revealing Rachel’s collection of knickers. He knew the pair he had wanted so he picked them up and analysed them. The white, soft and thin with lace lining around the leg along with the tiny ribbon bow design on the front gave his chills. He let his bathrobe slide off of his shoulders, crumbling around his ankles, leaving him bare and naked.

He stepped into the panties and pulled them up his legs, feeling the soft cotton caress his legs in the process as they fit snugly around his waist and behind. He felt so bad, so perverted, yet natural and serene. He turned and opened the second drawer where Rachel kept her socks and tights. He pulled out a pair of thin black high waisted tights. He had never worn these before so it was exciting to step into the legs and pull them up his shins, over his knees, stroking his thighs and up above his waist. It was a lovely feeling of softness and femininity as they hugged his legs comfortably yet tightly.

He walked up and down the room for a moment, wiggling his toes against each other within the tights. He shuddered and smiled and he went back to the chest, opening the third drawer which was filled with a wide array of bras ranging from training bras to push up ones. He picked up a white push up bra and stroked his fingers along the soft padding, the frills around the top lining and the extra push support. It gave off the essence of pure femininity and maturity.

For a moment he wondered what it would be like to have real breasts then he wondered WHY he wondered that?

He picked up the warm freezer bags and expelled the air from them. He then tied them around his neck and placed the bra upon them. Again, he had great difficulty in finding the straps on his back. When he did he tightened them hard, suddenly feeling the sensation of what it would really be like to have boobs. The slight weight, the feeling of the straps on his back and seeing two mounds on his chest made him feel somewhat . . . girly.

‘’And now for the best part!’’ he said to nobody in particular.

He opened the fourth drawer to see it packed with dozens of skirts, shorts and more tights. He wondered why a girl needed to have so many skirts but then he thought that he would have probably been the same if he was one. He rooted through the drawer, not noticing his heavy breathing of anticipation as he searched for the one he wanted.

After a few moments he found it lying there in all its glory, waiting to be worn once again. He touched it and held it up eyelevel. It was designed to be worn high above the waist, short and cute. It was pleated, short and light pink with a black frilly underskirt. The main attraction of the skirt was the large black bow which was tied neatly to the front of the waistband belt.

Charlie had only seen Rachel see it once and ever since then he had fantasised about wearing it for himself. Now it was about to come true.

He stood up and stepped into the skirt and pulled it slowly up his legs. It seemed that his legs would go on forever as the skirt fabric brushed against his thighs. The waistband went all the way up past his bellybutton lengthening only halfway up his thigh, just about hiding his behind.

He then went to the fifth and final drawer, opening it and staring into its wide collection of t-shirts, blouses, camisoles, tank tops and vests. He dug in and grabbed a grey tank top that would match his tights perfectly. He lifted it up, noting the revealing curved neckline to tease cleavage and its sleeveless arm revealing gaps. He couldn’t remember the last time Rachel wore it, maybe she never did, he couldn’t remember.

He pulled it over his head with great difficulty. It was very tight and hugged his false breasts snugly. He tucked the tank top into the skirt and zipped it up, encasing his entire body in the girly outfit. He then walked to the makeup station, feeling the roomy, free feeling of the short skirt flare against the gentle movement.

He wore a goofy smile on his face. He couldn’t help it. He was just so happy. He sat down in front of the makeup desk eyeing all of the tubes, tubs and boxes filled with lipsticks, eyeshadowers, eyeliners, kits and lotions. His chest was moving in, out, in, out as if he were staring at the most incredible sight ever. He didn’t know if it was safe. He didn’t know if Rachel would notice. Should he take the plunge and try on makeup for the first time? He had been reading through websites which instructed on how to apply makeup perfectly.

He looked around himself to make sure nobody was there, just in case. He looked back at the station feeling anxious and nervous.

‘’I guess a little bit couldn’t hurt,’’ he said to himself.

His hand was shaking slightly as he touched the round black capsule which contained the foundation. He grasped it and opened the thin lid. He looked over his shoulder again, nobody was there. He didn’t know why but he kept thinking that he was being watched by somebody hiding in the room. He brushed it off as paranoia and returned to his more ‘’important’’ thoughts.

He racked his brains to remember the step-by-step guide on how to apply makeup properly. Then he remembered that he needed to moisturise first. He looked around the station and spotted the little plastic bottle filled with clear liquid. He squirted some moisturiser into his hands and rubbed it gently onto his cheeks, nose, neck and forehead. The liquid soaked into his skin pores, leaving his skin clear and hydrated after a few minutes of waiting. He then wiped away any excess grease.

Charlie then dotted foundation on his nose, chin, cheeks and forehead. His hand trembled as he picked up the foundation brush and raised it to his face. As the bristles touched his face, he suddenly felt different. He began to feel and even act like a real girl. It was a most strange feeling for him. He looked in the mirror, blending the foundation carefully as if he were painting a masterpiece. After that he began to spread out the foundation with his fingers, and then finishing with a moist sponge to add final touches.

He kept repeating, ‘’blend, blend, blend’’ under his breath as this was key to having perfect foundation.

He decided to skip the eye shadow and instead only apply the dark eyeliner. This took him a very, very long time to perfect. He found it difficult to keep his eyes still. He kept blinking and his hand trembled because of nerves. After a while he managed to perfect it to the best of his abilities.

He then added pink blusher to his cheeks to bring out a healthy rosy look followed by the careful application of lashes which also took him quite a while to perfect.

Once he done he couldn’t believe how much he looked like his sister. In some ways it disturbed him yet in other ways it made the hairs stand up on the back of his neck. He couldn’t take his eyes off of his reflection. ‘’That’s not me, it couldn’t be me!’’ he kept whispering to himself.

He touched his busted chest and then stroked the fabric of the tank-top. His eyes were then drawn to a pink hairbrush as if it had just called out to him. He picked it up and began to shakily brush his longish hair. The bristles stroked through the knots and clumps of hair, pulling out strings of brown whilst softening and lengthening it into a soft glowing doo. He brushed for a while, not taking his eye off of his reflection in the mirror.

Within moments he had fixed his hair hung down past his ears, gently touching his shoulder like a soft velvet curtain. He sighed, feeling disappointed that his hair didn’t look as feminine as the rest of his face and body. It wasn’t thick enough but it was still passable as a teenage girl’s hair. He fixed the fringe and held his hair back with a yellow band.

He didn’t want to chance applying the false nails in case Rachel would notice but he put some bangles on around his wrists and wore a silver heart pendant. He then got up and went for the door. He listened carefully before setting foot out into the rest of the house in case anybody was there.

The door creaked as he opened it and he walked out into the hallway. He didn’t know what to do now. He pondered on what to do next. What could he do? He was most certainly not going to go outside. He may have been free to try on his sisters clothes all day but he was still restricted within the confines of the house.

He took a step forward, feeling the cushiony softness of the tights between his toes. He randomly jumped in the air. His hair flopped freely along with the skirt. He laughed to himself as a grin slowly formed across his face. Then he felt a little silly.

He looked down at his feet wishing that he had some girl shoes but his sisters ones didn’t fit. Then a quick thought flashed across his mind. He turned to his mother’s bedroom door, his mouth hanging open as he stared at the handle. His heart began to pound and his body electrified with delight.

He walked into his mother room. It was draped with dark purple curtains and matching bed sheets. The floor was carpeted with soft furry wool that was simply blissful to walk on. Like Rachel, she had a makeup station and a chest of drawers. The walls were covered in chocolate brown stripped wallpaper that gave the room a soothing quality. There were pictures of Charlie and Rachel throughout their lives hanging on the walls.

He looked at a picture of himself, Rachel and his father. He stared into his father’s beaming face with an expression of bitterness and woefulness. He wondered what his Dad would think if he saw him right now, in his ex-wife’s room about to try on her shoes. He quickly looked away as he thought this, feeling that his focus was being directed elsewhere.

He went to his mother’s walk-in wardrobe. It was a massive closet, filled with clothes she has worn once or twice throughout her life. Under the rails were shelves filled shoes, slippers, runners, boots and high heels. He began to look through the massive array of shoes, carefully putting them back in there right place. They were all two sizes too small for his feet. He began to feel frustrated. He continued to search through the dozens of shoes, coming across some beautiful pairs of heels that he would love to wear but like the rest they were all too small for him.

He gave up and sat on the ground feeling hot and flustered. He took several deep breaths before noticing an unopened shoebox stuffed underneath a pile of random single shoes. He leaned out and pulled it out from beneath the stack. He opened the box to find a pair of unworn black ankle boots. The heel was four inches long with a decorative bow on the outer side of each boot. His eyes sparkled as he looked down into the box. They were perfect! But did they fit him?

He took them out of the box and placed the sole of the boot against his foot. They fit! But they were slightly smaller. He began to smile once again. Not only had he found a pair cute of high heeled boots that fit him but they also complimented the rest of his outfit perfectly.

He remembered his aunt had bought them for his mother about two years ago as a birthday present but they were obviously too big for her and she stated that she was too old for ‘’ankle boots’’.

He walked back into his mother’s room carrying the shoes and sat on the bed. He lifted up his right foot and put it into the shoe with great difficulty. He strained to get his foot right though the hole. He gritted his teeth as his arms shook. Then his foot fell in with ease. His heel touched the inside snugly but his toes were slightly cramped. He did the same with the other and within a moment he was wobbling about the room in his new high heeled boots.

He chuckled to himself out loud as he looked down at his feet. He felt so much taller yet very girly at the same time. It didn’t take him long to stop swaying from side to side. He smiled as he looked at himself in the full length mirror. He placed his hands on his high waisted skirt and performed a curtsey to his reflection, batting his eyelashes and smiling coyly. He began to feel warm from head to toe as his cheeks turned scarlet, embarrassed by his dainty appearance.

He felt that his outfit was missing something. He looked at the tank top tucked nicely into the waistband and wondered what was overlooked when he was changing into the outfit. He clicked his fingers as it dawned upon him. To truly complete his garb he needed a jumper or a jacket.

He left his mother’s room and walked back into Rachel’s room. He didn’t wobble but his walk needed a lot of practising in order for it to look anyway womanly. He opened his sister’s wardrobe and browsed through the various coats, jumpers, sweaters and jackets hanging from the rails. He glanced through several garments before finding the adept jacket to compliment his outfit. It was a light pink blazer with a black outline around the collar and cuffs. It had rolled up sleeves with cuffs and a short tail at the back. It matched his pink skirt, black tank top, tights and heeled boots sublimely.

He put it on without difficulty. Suddenly, he felt whole. He looked like a true girl and intermediate feelings of awe and fear churned within him. Awe at how much he resemble his sister and fear of being caught. He had basked deeper than last time, the makeup, the heels, the skirt and tights. It was too much for him to comprehend.

He stared into the full mirror feeling flustered and decalescent. His chest pushed in and out as his breathing accelerated. His eyes began to water as if he were staring at a firework display. He touched his cheek and gasped breathlessly.

‘’It’s me,’’ he whispered silently.

A wide grin slowly spread across his face and within seconds he was strutting up and down the hallway as if it were a catwalk. His ankles nearly bent a few times but he didn’t give up. He wanted to perfect his walking with heels. His only wished that he had an hourglass figure just for the day.

He walked around the house with his shoulders thrown back and his pelvis pushed slightly forward. However he wasn’t pleased. He picked up a cookbook from the worktop in the kitchen and placed it on his head. It fell on the ground dozens of times before he managed to gain balance. He walked from the kitchen to the sitting room to the dining room, his skirt swaying from side to side and his hair bouncing slightly.

He continued to practice his walk over the next few hours. He learned to put his heel first before his toes. It felt strange but it wasn’t long before he developed an elegant stride. He couldn’t help but feel giddy as his feminine walk formed. His arms swayed back and forth naturally, close to his sides and the fingers still.

And before he knew it hours had passed and it was almost three o’clock. With his mother and sister not home until eight o’clock that evening he still had hours left to try on other clothes. He ran (yes he ran in heels) up the stairs smiling cheerfully, excited on what was to come. He went into his mother’s room to take off the heeled boots.

He took one last look at his outfit before sitting on the bench in front of the makeup station. He placed his hands on the boots and began to pull. They were nearly impossible to take off. His thin arms shook under the strain of moving his foot out of the shoe. His face turned red as he felt his heel slowly slide up.

Suddenly, he froze and all colour was drained from his face as he heard echoing footsteps from the corridor approaching. Louder, louder, LOUDER!

‘’Charlie, I’m home!’’ called his mother’s voice. ‘’I just thought I’d check up on you during my lunch break!’’

A massive weight plummeted to the very pit of his stomach as his heart crawled up his throat. A tidal wave of terror crashed upon him. He literally couldn’t move. He had no idea know what to do.

Poor Charlie, he was so scared.