Summary: Charlie is a normal teenage boy with a deep desire to dress in his twin sister’s clothes. It first starts with him trying on her school uniform but then his craze develops into something so much more as the pleasurable sensations of female clothing takes him into its warm embrace. It becomes something of a risky addiction. This series of episodic chapters will chronicle his fascinating journey into becoming a young transvestite from the beginning until the very end.

Charlie stared at the door as if it were a wave of fire rapidly heading toward him. His eyes watered and his hands trembled with shock. His could hear his mother’s heels clicking against the shiny wooden floor getting louder and louder as she approached her bedroom door.

Then, something electric shocked Charlie’s brain which broke him free from his frozen state as adrenaline pumped through his body. He jumped to his feet and turned for the walk in wardrobe. His fear gave him incredible agility as he dived for the closet door. His mind was in a state of gloaming as if he could no longer think. It was as if his body was working itself and he was the passenger.

As the bedroom door swung open the closet door shut concurrently. His mother stepped inside the room and looked around with her hands on her hips. She was dressed in her waitress uniform with a long tanned trench coat wrapped tightly around her torso.

‘’Charlie?’’ she said softly as she looked at the closet door. ‘’Are you in there?’’

Charlie placed his hand over his mouth as his eyes welled tearfully. For the first time in years he thought he was about to cry his eyes out in terror. He stood in the dark closet, unable to see anything through the pitch blackness, as he broke out in a cold sweat.

His mother’s brow arched with confusion as she approached the closet door and reached out for the knob. The lock clicked and she slowly opened the door. All she could see was her wide array of outfits and clothes hanging from the rails on each side. She stepped inside and looked around with a perplexed expression on her face.

Charlie hid behind the clothes hanging from the rails looking utterly perturbed as he held his breath. He could just about see his mother standing with her hands on her hips through the dresses. The only thing he could hear was his heart palpitating to dangerous heights. His knees shook erratically as drops of sweat dripped down his forehead.

His mother raised her eyebrows in dismissal and turned to leave. She closed the closet door and all light was sucked out of Charlie’s vision. He continued to anxiously hold his breath until he heard the thump of the bedroom door closing.

‘’Charlie!’’ called his mother once again as she walked down the hallway.

He gasped for breath and clenched his chest with relief. He got out of the clothes rack and continued to inhale air as if he was just pulled out from beneath water. But he wasn’t in the clear yet. He had to get somewhere safe to take off the outfit. In the darkness he pulled off the heeled boots with all his might. He couldn’t see a thing so he pulled the cord which turned the light on. He scurried on the floor, searching for the shoebox as if there was a ticking time bomb about to explode. He found the box, placed the ankle boots back inside and put it back under the corner pile of shoes.

He then jumped to his feet and listened carefully. He couldn’t hear a thing. For all he knew his mother could be still right outside the bedroom in the hall. He bit his lower lip nervously, racking his brains on what he should do. He got down on his knees and pressed the side of his head against the carpeted floor. He could just about hear his mother’s muffled footsteps downstairs. He then picked himself up to his feet and slowly pushed the door open. He stepped out into his mother’s room and ran to the door. His tights against the carpet floor made very little sound. He then pressed his ear against the bedroom door. Nobody was in the hallway. He carefully pushed down the handle and opened the door. The slight creak made him cringe with fear before he finally shut it closed.

‘’Charlie, where on earth are you!’’ bellowed his mother’s voice angrily.

He tip-toed down the corridor like a burglar, the soft feeling of the tights against the polished wooden floor made everything easier. His heart was literally in his throat as he approached his bedroom door. Then, he froze stiff as he heard his mother climbing the stairs.

‘’S-Sorry mom, I was in the bathroom!’’ he bellowed down the corridor.

His mother only replied with her rapidly approaching presence. She was obviously very angry with him. He acted fast and broke into an agile sprint towards his room. Within a second he slammed his door behind him and dived for the bed. He pulled the blankets over his entire body up as far as his neck and turned his back on the door. Just before his mother entered the room he managed to pull the hair band out and ruffle his soft doo back to his shaggy state over his half his face.

His mother opened the door, flicked on the light and stepped through. Charlie let out a moaning groan of sickness.

‘’Charlie, what the hell’s the matter with you? I called you over a million times!’’ she said as she approached his bedside.

He was beneath the blankets praying that his mom didn’t see his face covered in his sister’s makeup. The tension was so great that he could barely talk back to her. She placed her hand on his shoulder and shook him gently.

‘’Charlie, are you feeling okay?’’ she asked softly.

‘’I just wanna sleep,’’ he breathed out tiredly.

His mother didn’t say anything for a moment before whispering, ‘’okay honey, I just thought I’d check up on you. I’ll be home again later tonight’’ and then she left.

Charlie waited in bed for the next half hour staring into a trance. He was thinking about his cross-dressing secret and how it was affecting him as a person. When it began he had only wanted to try on his sister’s uniform just once and no more. He was just a little curious. Before then he had no interest in wearing anything else, just the uniform. But since that day a few weeks ago he had unlocked something which was obviously buried deep within. His curiosity changed into desire and his desire was slowly changing into an addiction. Despite the fact he was almost caught twice he still wanted to continue driving his fantasies.

‘’I was almost caught,’’ he whispered to himself.

He blinked for the first time in over a minute. Wetness squeezed out from between his eyelids as he blinked. He licked his lips and took a deep breath through his nose.

Even though he loved doing it he knew he had to give up dressing in his sisters clothes. It was much too risky. He was almost caught on both occasions and they were the first times he cross-dressed! He scoffed to himself as he thought ‘’Jesus I really suck at this!’’ and he turned in his bed.

He could hear the engine of his mother’s minivan jerking before starting up and reversing out onto suburban cul-de-sac. He was alone in the house once again. He threw the blankets off and went to his sister’s room to undress. He made sure there was no scent left and that everything was placed back to their rightful positions before heading to the bathroom with a bottle of makeup remover. He used only a small fraction on his face in case his sister noticed. It took him ages to get everything off, especially the eyeliner and lashes. He spent over a half hour just ridding the jet black substance from his lashes. Miraculously, when he was done there was not a single shred of makeup evidence left on his face.

He sighed with relief as he stared into the mirror above the sink. He looked into his own eyes. The pupils swirled about within the colourful green, frightened yet relieved.

‘’No more cross-dressing,’’ he said to himself.

He then left the bathroom to hang about the house for the remainder of the day.

***

The clouds hang darkly above suburbia. The sky is painted with whites, greys and blacks. Everything is dry yet crisp and dull. There is little sunlight, only grey as a light chilly breeze lays about the streets. Cars pull out of driveways as the people of Saulsbury Lane leave their homes to go to work and school.

Charlie and Rachel leave their home through the front gate. Both are dressed in their school uniforms with their bags thrown over their backs as they set off for another gruelling day at Castlemore Community School. Charlie is attired in his usual blue sweater, light blue shirt, dark grey tie and pants with a pair of white sneakers whilst Rachel is dressed primly in the same school uniform that her twin brother had once tried on.

Charlie yawned like a lazy lion. His eyelids felt heavy against his sleepy eyes. Rachel however was wide awake, standing upright and clenching her books to her chest. They walked together in silence as usual. The school was just under a mile walk but it felt like ten each and every morning.

They made as far as the cul-de-sac sign before turning alongside the main road. Suddenly a car pulled up beside them. It was a small but sporty blue ford fiesta. The window rolled down and loud music spilled out onto the pavement. Charlie wondered who it was but Rachel obviously did as a she dramatically changed mood.

‘’Hey Rachel, ‘sup Charlie!’’ said Dave O’Donnell leaning out from the driving seat.

‘’Hi Dave!’’ said Rachel, giddy and excited.

Without saying a word to Charlie she got in the passenger seat and put on her seatbelt.

‘’Oooh you got a new stereo!’’ said Rachel, reaching out to touch it.

‘’Careful babe, its brand new!’’ he smiled crookedly, trying to not look bothered. ‘’I’ll see you later Charlie!’’

And then he shifted it into gear and zoomed off down the road leaving Charlie behind. He looked at the car as is slowly shrunk in the distance. Dumbfounded, he muttered and cursed to himself like a crazy old man.

‘’Oh no it’s okay. I enjoy walking to school early in the morning. No need to offer me a lift in your empty car!’’ he muttered sarcastically.

Charlie met up with his best friend Sean outside his house along the way. They walked the rest of the way together.

‘’Where in god’s name were you yesterday? You missed so much!’’ said Sean.

‘’How is it that every day I’m out something incredible happens at school?’’ said Charlie, knowing well that Sean was lying.

‘’No man it was great! Young Alan finally ticked and went ape shit on Gary. He punched him straight in the face and he fell backwards on his ass! It was priceless!’’

Charlie scoffed, raising his eyebrows, ‘’Huh, so young Alan finally ticked? I never thought he had it in him.’’

‘’That was exactly everyone else’s reaction. I’ve bet my lunch money that he won’t be in today,’’ said Sean.

‘’In fairness though, Gary had been bullying him for the past year,’’ stated Charlie.

‘’He’ll certainly have a harder time now,’’ said Sean, the smile slowly vanishing from his face.

‘’Poor young Alan,’’ said Charlie, shaking his head.

The two boys reached the school building within a few minutes. It was large, brown-bricked and looked as if it were built in the 1980’s. It was situated near the town centre and at this particular part of the morning the streets were swarming with blue school jumpers.

Charlie and Sean walked up the entrance steps and walked through the main corridor. The school had four levels and was painted brightly along with decorative trophy cases and class photos hanging on the walls. The main corridor was wide, spacious and was scattered with many students. An array of lockers stood against the walls on each side of the hallway with a drinking fountain wedged at the end of each side.

‘’Awh no look! The fat bastard came in!’’ groaned Sean, stopping in his tracks.

Charlie turned his head to see what Sean was looking at, Young Alan, a massively tall and overweight boy with thick rimmed glasses and a plump red face.

‘’A minute ago you felt bad for the guy and now you’re calling him a fat bastard?’’ said Charlie, trying to make sense of his friends empathy.

‘’Yeah but that’s not the point man, he’s cost me my bloody lunch money!’’

Suddenly, the loud bell drilled into each and every student’s skull making some but not all groan with reluctance. The corridors were suddenly packed with blue jumpers as everybody scattered to their classes. Charlie had double woodwork first thing. He sat through it with difficulty, feeling bored and impatient with his teacher’s low droning voice. Every class was the same. He sat through it, daydreaming and fidgeting with his pens. For some unknown reason not even his favourite classes interested him today.

He sat through English staring out the window down at the fresh green grass. Having classes on the top level of the school offered an excellent view of the distant city skyline. He was thinking about the day before. How he was close to becoming caught by his mom. He couldn’t even bring himself to think of what she would say to him. Would she be angry, supportive, amused or concerned? She always held him in such high esteem and he was beginning to realise that he should never risk cross-dressing again. Then again, was there truly anything wrong with it? It was just clothes after all. Charlie didn’t want to believe that he was a ‘’cross-dresser’’. He believed that he was just curious. But curious so much that he had done it a second time?

He looked down to see a large group of girls dressed in their tennis uniforms as they made their way back from the courts. The short white pleated skirt, the short sleeved polo shirt, the white knitted vest and the soft cotton socks sent shivers down Charlie’s spine. What he would give to try on that outfit!

‘’Charlie, Charlie, CHARLIE!’’ whispered Sean from the desk beside him.

He snapped out of it and turned to Sean, dumbfounded and confused.

‘’Kavanagh, the answer is Kavanagh!’’ he whispered.

Charlie quickly turned his head to the front of the class to see everybody’s eyes looking at him. The teacher was strutting angrily towards him with an infuriated expression on his face.

‘’Kavanagh sir!’’ said Charlie aloud and confidently.

‘’Too late!’’ bellowed Mr. Wilson savagely before slamming his fist down upon Charlie’s wooden desk.

That lunch Charlie, Sean and Joseph sat on the park benches in the back of the school. Joseph was a tall lanky black haired boy with a long face and high cheekbones. He was what you would call a characteristic dim-wit who was always happy and cheerful. He was better friends with Sean than Charlie.

‘’Christ that Mr. Wilson is psychotic!’’ stated Sean. ‘’He should be in a mental home the way he acts!’’

‘’Who’s Mr. Wilson?’’ asked Joseph, squinting as if he couldn’t see quite well.

‘’He has been your English teacher for the past three years you twat!’’ said Sean.

‘’Is that his name?’’ asked Joseph.

‘’At least he let me off with a warning this time,’’ mumbled Charlie.

Sean and Joseph had a tasteful conversation about ‘’shifting girls’’ the proper way whilst Charlie wandered into yet another daydream. He looked around the vast school yard to see students scattered in packs all over the place. In the distance he could see Rachel and Dave cuddling by the tree. He immediately looked away as it sickened him to see his sister in such a light. His eyes then trailed to a group of girls in the distance. He was staring at their skirts, wishing that he was wearing one right now. He then shook the thought away and thought to himself, ‘NO Charlie! You’ve given up that stuff! It’s time to move on!’’.

As soon as the bell went the three boys made their way to their third and final period of the day. They squeezed in between the hoards of pupils in the wedged corridors. As Charlie walked around a corner he bumped into Julie, a pretty red haired girl with piercing green eyes. He suddenly felt as if he were back hiding in the closet from his mother as his heart began to pound fiercely against his ribs.

‘’Oh h-hey Julie!’’ he stammered.

Sean, who was standing behind him, rolled his eyes as he knew that Charlie had liked Julie for some time now.

‘’Hi Charlie! I haven’t seen you all day!’’ she smiled warmly.

Her voice was soft, squeaky, and high pitched but above all else hypnotising.

‘’Yeah I’ve been with these losers!’’ joked Charlie, gesturing to Sean and Joseph.

Julie’s girlfriends behind her had the exact same expressions of disgust as Joseph and Sean as they watched their friends nervously flirt.

‘’Well, I’ll see you later then,’’ smiled Julie pleasantly.

Charlie nodded and smiled. She then walked by him followed by her friends in tow.

‘’When are you gonna ride that one?’’ asked Sean rudely.

‘’Will you shut up!’’ snapped Charlie.

‘’Ooh alright! Getting all defensive over your wimpy little crush!’’ in a fraudulent tone. ‘’Ask her out already. The girl obviously likes you!’’

Charlie didn’t respond. He was still flinching after the awkwardness of the encounter with the girl he liked, Julie O’Sullivan.

***

Later that evening Charlie sat down for dinner with his mother and Rachel. It was usual for Charlie because he hadn’t sat down to dinner with Rachel and his mother, Mary, since his Dad left them. Charlie was in high spirits because he was having his favourite meal, BBQ spare ribs, tacos and fries. It was amazing how much better it made him feel. His mother was obviously trying to bring back some sort of a family atmosphere to the house.

‘’ — the amount of foreign nationals going back to their home countries is crazy. Mr. Johnson is slowly loosing staff in the restaurant and he will soon have to put an ad in the paper for extra dishwashers,’’ said Mary, using her fork as a pointer. ‘’If you want I could put in a good word for you two. You’re both old enough for part time jobs now.’’

‘’Eww no, washing dishes in some back kitchen, no way!’’ said Rachel, wrinkling her nose in disgust as she raised a chip to her mouth.

‘’Once you start college you’ll take any job you get young lady, believe that!’’ said Mary, pointing her fork at Rachel. ‘’How about you Charlie?’’

‘’Oh, well I dunno, I wouldn’t have any time off if I start a job,’’ said Charlie honestly. ‘’What with school, homework and such.’’

‘’It would only be part-time. Every Friday and Saturday night,’’ smiled Mary reassuringly.

‘’Um, I’ll think about it Mom, I will.’’

‘’Well don’t think about it for too long. Part-time jobs are scarce in times like these,’’ said Mary as she tucked into her dinner.

The three sat in silence for a few moments. The only sound to be heard was the clinking of cutlery and the television blaring from the neighbour’s house next-door. Rachel opened her mouth to speak.

‘’Hey have you um— uh — oh,’’ she said, forgetting what she was about to say midsentence.

Mary and Charlie looked at her, waiting for to say something.

‘’Oh yes, um have you been using my makeup?’’ said Rachel, looking down at her tacos.

Charlie suddenly felt as if he was thrown into a pit of lava. His entire body suddenly felt over heated and his skin suddenly became sticky with sweat. Was she talking to him?

‘’Mom?’’ she added, looking over at Mary.

‘’Oh, well yes I used a little bit a few days ago because I ran out of foundation,’’ said Mary as she cut her meat.

Even though Rachel hadn’t directed the question at Charlie he didn’t feel anyway relieved. He was on high alert and he had suddenly lost his appetite. He got up from his seat and took his plate in his hands to the bin.

‘’Where are you going?’’ asked Mary.

‘’I’ve got a colossal amount of homework to do. I should get started,’’ lied Charlie.

‘’But we’re having dinner,’’ said Mary as she watched her son throw the leftovers into the bin.

Charlie could feel himself beginning to get angry. A horrible creature lurched inside his chest ready to lash out at somebody.

‘’I know Mom but like I said I have a lot of work to get done,’’ said Charlie, gritting his teeth as he placed the plate and cup into the sink.

He then left the kitchen, went upstairs and locked himself in his bedroom. Rachel looked at Mary and shrugged confusedly. Then the sound of a horn honking echoed from outside the house. Both Mary and Rachel looked towards the door.

‘’That’s Dave!’’ beamed Rachel from ear to ear.

She jumped up from her seat, emptied her scraps into the bin and put her plate into the sink.

‘’Where are you going?’’ asked Mary, her eyes wide and watery.

‘’I’ll be back soon Mom I’m just going out with Dave!’’ said Rachel, unable to control her giddiness.

Mary’s eyes followed Rachel to the coat hanger. She looked and felt incredibly hurt.

‘’But — the family dinner it was our idea to -,’’

‘’I’m so sorry Mom. I forgot to tell you. I’ll be back soon, I promise!’’ said Rachel, zipping up her coat.

Mary watched her daughter leave the kitchen. The sound of the front door slamming and the blue ford fiesta zooming away made her lower lip tremble. She then buried her face into her hands as she sat alone at her family table, crying her eyes out.

Meanwhile, Charlie was lying on his bed with his laptop resting on his laps. He opened a tab for Facebook and another for Google. He sat staring at the empty search bar, pondering and what to do. He was frozen and expressionless for a few minutes before typing ‘’cross-dressing’’.

11,200,000 results.

He raised his eyebrows and scrolled down through page. An advertisement on the side of the page read ‘’Sex Personals Connecting Cross Dressing Fetish Playmates for Fun’’.

‘’Is this what I’ve become?’’ he wondered. ‘’Something strange happening to me, I’m not the person I used to be.’’

He clicked into a cross-dressing store website and scrolled down through the many products up for sale. Body shapers, breast forms, wigs, masks, body suits, fake nails, lashes, makeup, outfits, costumes and corsets all at expensive prices. He sighed and closed the tab to see that he had a chat message of Facebook.

Julie: Hi Charlie! :) x x x

He couldn’t help but feel warm inside. He smiled to himself as he prepared a message to send back to her.