A Boy With Girly Hair - Little Brother - Chapter 1

ALL STORY LIST | CHAPTERS - CH 2

When he looked back on it, Jack Burton was never entirely sure why he went into his sister’s room that afternoon.

It was probably, he thought, something to do with the troubles he was having at school.  Ever since he had decided to let his hair grow he had been bullied unmercifully.

It started when someone photo-shopped his picture onto a poster for the Ladyboys of Bangkok, they came to Brighton every year for the Festival and posted it on Facebook.

After that, everyone at school started calling him ladyboy, or sometimes girly-boy.

He pretended he didn’t care, but he did. His chief tormenter was a boy called Brad Phillips, who traveled on the same bus as Jack and never missed an opportunity to humiliate him.  Brad was a year older than Jack, a big, ugly boy with a shaven head who seemed to enjoy inflicting pain, both physical and emotional.

He was also a gifted footballer and captain of the school football team and thus was guaranteed a circle of admirers. One lunchtime he persuaded his cronies to hold Jack down while he tied a bow in his hair and then warned him not to take it out unless he wanted a beating. So Jack just stood in the playground with a big, floppy bow in his hair trying not to cry while the other kids stood around him in a circle laughing and jeering.

He was too frightened to take it out when the bell rang but he thought his ordeal would end when he got into a classroom; instead, the teacher of his first-class after lunch just smirked and said “I like your bow, Jack, very pretty” and the entire classroom erupted into laughter.  When the order had been restored, the teacher told Jack to take the bow out, but the damage had been done by then.

Everyone in the school soon heard what had happened. Brad, emboldened by the success of his great joke, had another trick up his sleeve the following day on the school bus. Jack knew something

bad was going to happen when he saw Brad whispering to two girls in front of the school bus and pointing at him. The girls were giggling, then one of them got up, followed by Brad, walked to where Jack was sitting, held out a lipstick, and asked him if he wanted to borrow it.  He shook his head and stiffened as Brad pushed the girl out of the way and leered “Yes you do, girly boy.  You definitely need some lippie.”

He turned to the girl and held out his hand and she gave him her lipstick. Jack started to get up from his seat to try and move away, but he was grabbed from behind and someone tugged on his hair, pulling his head back.  Brad twisted the lipstick, it was bright red and smeared it viciously all over Jack’s mouth.

“There, girls,” he said to the bus, “doesn’t she look pretty?”

Then he put his face inches from Jack’s and  grunted “If you know what’s good for you, you little fag, you won’t try and take it off before we get to school.”

Jack was terrified. The girl who had offered her lipstick was shame-faced and tried to give him a tissue, but was stopped by Brad.

“No, he doesn’t want to wipe it off.”

He sneered.

“He likes wearing lipstick, don’t you girly-boy?”

Jack said nothing.

“DON’T YOU?”

Brad bellowed in his face. He seemed to be getting angrier and angrier.

“SAY IT. SAY I LIKE WEARING LIPSTICK.”

Another girl sitting nearby tried to intervene.

“Leave him alone, Brad,” she said.

“Why are you always picking on him?”

Brad rounded on her in a fury.

“Just shut up, you, and stay out of this.”

He turned back to Jack.

“SAY IT, GIRLY-BOY. SAY I LIKE WEARING LIPSTICK.”

Jack thought at any minute he was going to make things worse by peeing himself.

“I like wearing lipstick,” he whimpered.

“No. No one can hear you girly boy. Say it louder.”

Jack took a deep breath and shouted “I LIKE WEARING LIPSTICK. NOW ARE YOU SATISFIED?”

And I burst into tears.  Brad was delighted to get such a reaction. He pretended to be contrite, put an arm around Jack, and said “There, there, girly-boy, don’t cry.

Bradee will look after you” and then he suddenly grabbed Jack’s ear and twisted it hard, making Jack yelp with pain.  Most of the other boys on the bus apparently thought this was hilarious.  The girls mainly looked embarrassed, but no one moved to help Jack.

He sat there for the rest of the journey with lipstick all over his face, the sweet sickly taste in his mouth. As soon as the bus arrived at the school gates he grabbed his backpack and ran inside to the boys’ lavatory, where he did his best to scrub the lipstick off his face before too many people could see him. It was not the end of his troubles that day. At lunchtime, he found someone had left a dirty bra hanging on his locker with a note saying,

“Hey, ladyboy, this must be yours.”

He screwed it up and threw it away, along with the bra, but not before half the school had seen it and no doubt, he thought, had a good laugh. On the bus going home the girl who had offered Jack her lipstick apologised.  She claimed she had no idea what Brad was planning to do and said she was really, really sorry.  Brad was a pig, she added, and all the girls hated him. Jack airily pretended that he was not bothered by what had happened but he could see the girl did not believe him.  She smiled and touched his arm and said “Anyway, Jack, I’m sorry, OK?”

Jack nodded gratefully. Jack was 14 and had been at the Beacon Academy in Brighton for nearly three years.  He hated it, hated every moment.  He was sure that most of the teachers knew he was being bullied but none of them seemed willing to do anything about it.  His mother kept offering to go in and talk to the headmaster, but Jack knew word would get out and only make things worse so he dissuaded her. Jack’s problem although he would never admit it was that he was pretty.

He had auburn curly hair, flawless skin, a heart-shaped face, and big green eyes.  His aunt Sarah his mother’s sister never visited without saying at some point that he was too pretty to be a boy, particularly after he let his hair grow.  His Dad used to nag him all the time, making stupid jokes

about standing on his hair and hairdressers going on strike. But the more his Dad nagged the more determined Jack was not to have his hair cut.  Lots of other boys at school had long hair, he told his Dad, so why couldn’t he?

His father shrugged helplessly.

“If you want to look like a girl,” he once said, “I suppose it’s up to you.”

The Burtons lived in a large double-fronted Regency house in Kemp Town, on a road leading down to the seafront, on the east side of Brighton.  Both Jack’s parents commuted to London every day, his father, Mark, was the senior partner in a big advertising agency and his mother handled public relations for a property developer.

Neither of them ever got home before seven o’clock. Jack’s older sister, Emily, was training to be a beautician at Brighton Poly but always hung out with friends after class, so Jack was what the tabloids called a “latchkey kid”.

It didn’t bother him to come home to an empty house; in fact, he liked it.  He was supposed to spend the time doing his homework, but he rarely did. Mostly he sat at his computer playing games or posting stuff on social media.  Sometimes he watched porn and would sit staring at the screen with wide eyes as people did disgusting things to each other, things he never dreamed anyone would do.

He was amazed not only that people would do that, but they would do it publicly, in front of a camera, and then let it appear on the web.  He would often end up jerking off and then feeling weirdly guilty afterward.

When he got home on the day Brad Philips made him put on lipstick he wished, almost for the first time, that he had some company.  He did not particularly want to talk about what had happened, or what a wretched day he had had, but he would liked to have been able to talk to someone, even his sister, whom he cordially hated.

To their mother’s despair, Emily and Jack did not get on.  Emily, who was 18, liked all boys except her brother.  She made no secret of the fact that she thought he was a dork and Jack would respond that it was better to be a dork than a tart and then Emily would fly at him in a rage and their mother would have to separate them.

Still brooding over the “girly-boy” taunts he had endured at school, Jack went upstairs intending to change out of his school uniform but decided first to go into his sister’s room, where there was a full-length mirror.  He stood in front of the mirror staring at his reflection.

Did his long hair really make him look like a girl?

He put both hands behind his head to lift his hair up to see what he would look like if it was short and then giggled self-consciously, he looked even more like a girl with his hair held up and tumbling out of his fingers. His sister’s room was the usual mess, with her clothes all over the place, their mother always called it “the tip”.

She badgered Emily endlessly to tidy it up, but she never did. Jack noticed a crumpled denim dress on top of Emily's unmade bed. His sister had been wearing it the previous day.  He picked it up and out of curiosity held it against himself in front of the mirror.  If he put it on, he wondered, would he look like a boy in a dress or would he look like a convincing girl?

On the spur of the moment he decided he would find out.  He checked his watch: plenty of time.  Strangely hot and flustered, he took the dress into his own room and stripped down to his boxers. He could feel his heart thumping; to his surprise, he was getting a hard-on.

He couldn’t at first figure out whether he should step into the dress or pull it over his head and he had some trouble with the zip, but once he had got it on it felt perfectly comfortable. He went back into his sister’s room to look at himself and was immediately entranced.  He had never imagined seeing his legs protruding from a skirt but now he realized his long, thin, hairless legs were just like a girl’s. He could have stepped out the front door and walked down the street and he was more or less sure no one would have guessed he was not a girl.

It freaked him out. The dress had a tight bodice and short full skirt which swished slightly as he went downstairs. He just walked about the house for a few minutes, enjoying the sensation and the curious freedom of being in a dress.  He twirled to make the skirt flare out and laughed out loud.  He caught a glimpse of himself as he passed a mirror in the hall and smiled at his reflection.

He tried sitting down, on a leather sofa in the living room and felt the cold of the leather through his boxer shorts.  He stood up, tucked his skirt under his bottom, and sat down again.  He crossed his legs and let his skirt ride up a little, then demurely pulled it down.  He stood up again, uncertain what to do but reluctant to change back into his own clothes.

The realization that he was going to have to do just that very shortly saddened him and made him feel guilty.  He knew he shouldn’t be doing what he was doing, but he wasn’t sure why.  Why shouldn’t a boy put on a dress if he wanted to?

He checked his watch again.

Emily would not be home for at least another half an hour, but he did not want to risk being caught.  He went back upstairs, took a last look at himself in the mirror in Emily’s bedroom, then unzipped the dress and put it back on his sister’s bed, arranging it as closely as possible to the way he had found it.  In his own bedroom, he put on jeans and a T-shirt and switched on his computer.

He would normally have spent time on social media, but instead, he Googled “boys who look like girls” and spent the next hour trawling dozens of websites scrutinizing hundreds of pictures of boys dressing up as girls with varying levels of success.  He only switched to his Facebook page when he heard the front door bang and Emily shouted,

“Hey dorkie, I’m home.”

“Do you think I care?”

He shouted back. Jack could feel his heart beating as he heard Emily climb the stairs then go into her room and slam the door. He half expected her to burst into his bedroom waving the denim dress and accusing him of having worn it, but of course, she didn’t.  Nevertheless, he decided, definitely decided, that he would not do it again.

As he walked home from the bus stop the following day he reminded himself to stay out of Emily’s room.  He went straight up to his room, shut the door, sat down at his computer, and switched it on.  He stared at the flickering screen for a few minutes, then he suddenly stood up, crossed the landing to his sister’s room, and opened the doors of her wardrobe. Ten minutes later he had exchanged his boxers for a pair of his sister’s knickers

and was walking around the house in a tight black mini-skirt and striped top. It was like he couldn’t help himself, like an addiction he could not control. No matter how many times he resolved to stop in the next few weeks, he never did. He found himself hurrying home from school thinking only about what he would wear when he got home.  It was like he had a secret life as a girl; it was exciting and a bit risky. It even made the bullying more bearable.

He didn’t care now that Brad Phillips and his cronies called him “girly boy”, he just smiled to himself and thought if only they knew, Sometimes, if it was a day without PE or sport and he did not have to change out of his school uniform, he’d wear tights and knickers his own tights and knickers under his boxers.

He had realized that Emily would soon know if someone else was wearing her underwear so he had steeled himself to go into H&M to buy his own mumbling, scarlet-faced, to the sales assistant that he was shopping for his sister.  He had to be careful at school to keep his socks pulled up when he was wearing tights but as long as no one tried to wrench his trousers down he could get away with it. He also found a way to solve the problem of how to hide his parts.

Emily had about a dozen very tight, very short skirts that Jack particularly liked wearing, but he didn’t like the bulge that protruded in the area of his crotch.

He no longer got an instant hard-on when he slipped on a pair of knickers but in a tight skirt, you could definitely see there was something there. To his surprise, he found several videos on YouTube explaining various ways to tuck his parts out of sight.

He learned that it was possible to push his testicles up into his body, tuck his dick between his legs and hold it in place with two pairs of knickers or tights. He soon mastered the technique so that the front of his skirt was completely flat, even though at first it was extremely uncomfortable. Emily left her makeup scattered all over her dressing table and it was not long before Jack started experimenting with it, if for no other reason than it gave him something to do when he had got dressed rather than just walk aimlessly around the house.

He found it easy to apply lip gloss

and blusher, but eyeliner and mascara were more of a challenge.  He tried to put everything back where he had found it, although everything was in such a mess he could not believe that Emily would notice if stuff had been moved around.  He was wrong. He was sitting at her dressing table one afternoon wearing a floral cotton mini skirt, tights, and a white blouse trying to brush mascara onto his eyelashes when, to his horror, he saw in the mirror that the door behind him was slowly opening.  Standing in the doorway was his sister, her eyes blazing with fury.

“What the FUCK do you think you are doing?”

She shouted as she stalked into the room.

“I KNEW someone was going my things and it was YOU, you little pervert, you little shit.”

Jack opened his mouth to say something but no words came. He suddenly felt ridiculous. He had no idea what to do. He slowly put the mascara brush back onto the dressing table and stayed facing the mirror while his sister raged behind him.

“What the fuck do you think you are doing, coming into my room and helping yourself to my clothes and my makeup?

You’ve got a bloody nerve.

What are you?

Some kind of bloody transvestite?

Well, you can get your own dresses from now on.  You’re not wearing mine.

And you’re wearing my bloody tights, too. Christ.”

Jack, close to tears, mumbled: “I’m not wearing your tights.”

“Oh you’re not, are you?”

Emily sneered.

“Then whose fucking tights are you wearing?”

“Mine. I bought them for myself. And knickers.”

“You bought your own tights and knickers? Oh my God, my brother’s a tranny.  Wait till I tell Dad.” Jack, thoroughly alarmed, swiveled in his seat and turned to face his sister.

“Please, Em, please don’t tell them” he pleaded.

“You won’t do that, will you? Please don’t. Please.”

Emily had no intention of telling her parents, least of all her father, but she enjoyed making her brother squirm.  She looked more closely at his clumsy attempt at makeup and suddenly realized how pretty he could be.

The way Emily was looking at him made Jack very uncomfortable.

He stood up and made to go back to his own room.

“I’m sorry,” he said, “I’m really sorry, Em. I know I shouldn’t have done it.  I'll go and change. Please don’t be mad at me and please, please, don’t tell anyone. I’ll do anything you want if you just don’t tell.  Please, Em, please.”

“Shut up, Jack!”

Emily snapped.

“You’re such a fucking wimp.  I’ve got an idea. If you want to look like a girl, I’ll make you really look like a girl. Sit down.”

“I don’t want to look like a girl,” Jack protested. Emily laughed.

“You’re sitting there in a skirt with make-up plastered all over your face and you don’t want to look like a girl? Please.”

“No, I didn’t mean that. I don’t know what I meant.

Just let me go and change. I won’t do it again, I promise”

“You’re not going anywhere,” Emily said, now enjoying herself.

“I’m going to see if my little brother can really be turned into a girl. Sit down.”

Jack did as he was told. He could not understand what was happening.  He understood his sister being angry when she found him dressed in her clothes, but now she seemed unbothered.

“Don’t you want me to change?”

he asked uncertainly.

“No. You can keep that skirt and blouse if you want. I don’t want them after you have been wearing them.”

“Em, you won’t tell Dad or Mom will you?”

“For God’s sake, dork,  no, I won’t tell them.  Now sit down, this will be fun.”

As Jack sat back down at the dressing table, facing away from the mirror, Emily noticed how he tucked his skirt under him, just like a girl. She wondered how long he’d been helping himself to her things, but decided not to ask him.

“OK,” she said, “I will take off all your makeup and start again.

OK?”

Jack nodded and obediently followed his sister’s instructions look up, look down, close your eyes, and purse your lips for the next 20 minutes.

Emily hummed to herself while she sifted through the cosmetics on her dressing table looking for what she needed.  When she had finished his makeup, she brushed his hair until it shone then tied it in a ponytail with a red ribbon exactly matching his lipstick.

“Oh my God,” she breathed when she was done.

“You are hot.”

She swiveled the chair so that Jack could see himself in the mirror. He took one look and his mouth dropped open in amazement.

“Oh my God,” he said.

“OH MY GOD!”