A Boy With Girly Hair - Little Brother - Chapter 2

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Initially, Emily would have struggled to explain why she decided to help her brother dress as a girl, other than the certain knowledge that it would piss off her father if he ever found out. She had had a strained relationship with her father ever since she became a teenager.

It seemed to her she could do nothing right in his eyes; he was always moaning about the way she dressed, the way she talked, the boys she went out with, the money she spent on clothes, and the lurid, ever-changing color of her hair.

When he had given her a lecture about the dangers of casual sex shortly after her 14th birthday, she had deliberately lost her virginity the next night up against a wall with a boy she hardly knew. When he said he would give her £50 if she would promise never to smoke, she took the money and then came home after parties reeking of nicotine.

When he started nagging her about university, she enrolled at the local poly to train as a beautician because she knew what he thought was a worthless occupation. What really bugged her was that while she could do nothing right, her precious brother could do nothing wrong, even though he was a total dork. It was pathetic. Her dad pretended that Jack was like his best friend; that was what he always told his stupid friends at his stupid golf club when everyone could see that Jack was a total dork. Emily had once asked her mother, “Why does Dad think the sun shines out of Jack’s arse?"

Her mother had laughed and told her not to say anything like that to her father. Knowing that her father would be absolutely appalled to discover that Jack was dressing as a girl was more than enough justification for Emily, so she was happy to help turn her little brother into her little sister every day after school, if that was what he wanted. It gave her a weird thrill to see him in a dress.

When she first came across him in her bedroom in a skirt, she was so furious she could hardly speak, but once she saw that he really could look like a girl, she realized there was mischief to be made in helping him. She dreamed of getting him dolled up in a dress and full make-up and then walking with him into the bar at her father’s golf club.

That would be awesome. She was not quite sure how she was going to let her father know what was going on, but she was certainly going to do it somehow.

There was plenty of time. She wanted to wait until he had been transformed into what, exactly? Well, maybe someone who was as much a girl as a boy. Yes, that would be cool. Let’s see, she thought with malicious glee, if the sun still shines from his backside in a dress. Jack was incredulous when, a few days later, his sister came home early from college and announced that if he still wanted to dress up after school, it was OK with her if he borrowed a few of her things.

“But I don’t want you just helping yourself,” she said.

“I’ll put some stuff by for you to wear whenever you like, but if you want to borrow anything else, you’ve got to ask me first."

Ever since he had been caught out, Jack had not dared to go into his sister’s bedroom, let alone put on one of her dresses. He stared at her in amazement.

“Are you sure, Em?"

“Of course I’m sure. I wouldn’t have said it if I didn’t mean it."'

“You’re not still mad at me?”

"If I were still mad at you, I wouldn’t be offering to lend you some dresses, would I?"

Jack was silent for a moment.

“You don’t really think I’m a pervert, do you?” He asked anxiously.

“No, of course not.”

"Well, that’s what you said when..."

“Yes, I know, but I was angry. I wasn’t angry that you wanted to dress as a girl; I think that’s cool, but I was angry that you were just helping yourself to my stuff without me knowing.”

"But if I had asked you if it was OK, would you have said yes?"

“I dunno. I might have done."

Emily laughed.

“I’d rather have a sister than a dork. Come on, let’s find something for you to wear.”

Jack's heart leapt.

“You mean a dress?"

“No, a fucking boiler suit. You coming?”

Jack jumped to his feet and followed his sister into her bedroom. She rummaged among a pile of clothes on the end of her bed and pulled out a little black skater skirt and a crumpled pink top with a scoop neck.

“How about this?” she said. Jack nodded enthusiastically. He would have taken anything she offered.

"While you are changing, I’ll sort some stuff out for you, OK?"

Jack nodded again and took the skirt and top. He hesitated, unsure of what was going on; he suddenly wondered if his sister was playing some trick on him.

“Em,” he said slowly, “why are you doing this?"

“I told you,” she replied, without skipping a beat.

“I think it’ll be cool to have a sister for a change.”

Jack blushed furiously. God, Emily thought, he’s even prettier when he does that. While he was changing, she went through her wardrobe to choose things for him. She resisted the temptation to give him cast-offs that she would never wear again, stuff that she should have sent to the charity shop years ago, or what she called her “butch look” gear. She wanted him to look ultra feminine and ultra girly. When he reappeared shyly, she looked him up and down and smiled.

He was wearing black tights and Doc Martens, and the skimpy skirt only emphasized his wonderful long legs. For an instant, Emily suffered a pang of jealousy. No boy in a simple skirt and crumpled top, without a scrap of make-up, had the right, she thought, to look that good as a girl. He was almost pathetically grateful when she showed him what she had put aside for him and asked her if he could hang them in his own wardrobe, but she persuaded him that their mother only had to open his wardrobe doors to realize what was going on.

“I could tell Mom you were using my wardrobe for your overflow stuff,” he suggested, hopefully.

“She’ll never believe that in a million years,” Emily said.

“What I’ll do is tie a ribbon to the hanging rail in my wardrobe.

Anything on the “No, Em, I can’t. The neighbors might see me. And suppose we ran into someone from my school?

I have a bad enough time as it is, but if they found out I was dressing like this, my life wouldn’t be worth living.”

"Don't be such a wimp. I’ll give you a hoodie you can wear so the neighbors won’t recognize you as we leave the house, and if you see anyone you know, just turn your back on them."

“But supposing someone guesses I’m a boy?"

Emily laughed.

“Look at yourself in the mirror. Do you look like a boy? No. I can promise you, little brother, that no one is going to know you’re not a girl. Come on, let’s go for it. You can’t skulk around in the house all the time."

Jack was torn. A part of him badly wanted to do it, but at the same time, he was truly terrified. If it had not been for Emily’s insistence, he would never have dared risk it. Twice she got him to the front door, and twice he baulked, refusing to step outside, pleading that he needed more time to get used to the idea.

“Please, Em,” he said, "don't make me do it. I’m not ready."

“For God’s sake, Jack,” his sister snapped impatiently.

“I’m not making you do anything. Why are you being such a wimp?"

“It’s all right for you; you’re a girl, so it’s natural for you to go out in a dress, but it’s not for me.”

Emily had a motive for trying to persuade her brother to step outside dressed as a girl. She wanted to get some pictures of her brother out and about in a dress so that when the time came, their father would discover his precious son had not just been cross-dressing but had been walking around Brighton in a skirt. But the next step was to get him through the front door, and he was proving difficult. He insisted he could not do it, but Emily finally broke down his resistance by offering to lend him a dress she knew he coveted. It was a floral print mini dress she had bought only a week earlier from Monsoon.

"Oh my God, it’s gorgeous,” he said when she modeled it for him one afternoon.

“Yeah, it is,” she’d said, “but you can’t have it. It’s staying on my side of the wardrobe."

He had nodded and made a face. A week later, she asked him if he would like to wear it. “Oh my God, do you mean it?” he said.

“I’d love to."

“OK, but there’s one condition. You can wear it, but only if we go outside. It’s a nice sunny afternoon, perfect for a walk along the front."

Jack thought it was weird that his sister kept banging on about going out. Why did it matter so much to her? He had no idea. But he was longing to see himself in that gorgeous dress, and as long as he was careful, he thought, it would be worth the risk.

“OK,” he said hesitantly, “I’ll do it."

Emily had already done his hair and make-up, and in his own room, he changed into the Monsoon dress. It fitted perfectly. He went back into his sister’s room and checked himself in her mirror.

“Oh my God,” she said, “it looks better on you than it does on me."

Jack giggled and blushed. She rummaged in a drawer, pulled out a pair of green tights, and handed them to him.

“Here,” she said.

“These will look better than black. You can change here. I won’t look."

Jack, embarrassed, turned his back on his sister. He sat on the bed and took off his Doc Martens, then stood up, lifted his skirt, pulled down his black tights, and sat on the bed again to take them off, one leg at a time. He had long ago mastered the technique of putting tights on and taking them off. He rolled up one leg of the green tights and pulled it over his foot and up his calf; he did the same with the other leg, then stood to pull them up to his waist. He sat back down on the bed to put on his Doc Martens, then stood and smoothed the front of his skirt.

“That’s better,” Emily said, turning to face him.

“OK, are you ready?"

Jack nodded uncertainly. He could feel his heart thumping as he followed his sister downstairs.

“Em,” he said as they reached the hall, “I’m not sure I can do this. Can we do it tomorrow?”

“Don’t start that,” she snapped, lifting a hoodie off a rack on the wall and thrusting it at him.

“Put this on. You said you’d do it, and you’re bloody well going to, even if I have to drag you out the door."

Jack buried his head in the hoodie as Emily opened the door and pushed him out.

“We’ll just walk down to the front for a little while,” she said.

“As soon as we are away from the CTs, you can safely take the hoodie off."

Emily called all the neighbors “CTs” (curtain twitchers), although very few of the houses actually had curtains. As they walked down towards the seafront, Emily kept talking to him all the time, assuring him he had nothing to worry about and that no one would know he was not a girl. She told him to stop striding out, to take smaller steps, and not to keep looking around “as if he were a shoplifter in a department store."

He laughed nervously.

“It’s OK for you,” he said again.

"You don’t know what it’s like for me."

He did not want to admit to his sister that while he was terrified of running into someone he knew, particularly someone from his school, he was, at the same time, shivering with excitement at being out and about as a girl. He loved to see his long, thin legs in the green tights; he loved the way the breeze tugged at his skirt; and he loved the feel of the dress against his skin. When they reached the seafront, Emily suggested he take the hoodie off, but he shook his head.

“OK,” she said, “if you want to draw attention to yourself, that’s up to you."

Jack realized the truth of what she was saying. It was a warm afternoon; people would stare at him if he walked along hunched up in a hoodie. He pulled the hood off his head and shook his hair loose. Emily grinned.

“That’s better,” she said. They walked slowly, side by side, in the direction of the marina. Jack, expecting any minute to be exposed, could not stop himself from looking around furtively, but he slowly began to relax. There were few people about on a weekday, and no one paid much attention to two pretty girls out for a stroll by the sea.

He only had one moment of panic when they encountered a group of foreign students waiting for their coach. In the summer, Brighton was packed with school parties from abroad clogging the streets, and it seemed to Jack as they approached that the boys were all staring at him. He tugged at his sister’s sleeve and whispered, “Em, Em, why are they all staring at me?"

She laughed out loud.

“That’s what boys do, you dork. They stare at pretty girls and think about how much they would like to fuck them. If you want to be a girl, you’re going to have to get used to it, my new little sister."

Jack blushed; he did not know what to make of boys looking at him and thinking they would like to fuck him. But he liked it when Emily called him “little sister."

By the time they got home, he was high with the excitement of the outing, exuberant that he had stepped outside as a girl and no one had exposed him. Emily noticed as they approached their house that he did not bother to put his hoodie on; she wondered if he perhaps wanted the neighbors to see him. After that, they went out frequently, and Jack's confidence grew day by day. Emily took lots of pictures of him posing on the seafront, smiling broadly in different outfits, always in a short skirt with smokey eyes and cherry-red lips, often with the wind whipping at his hair.

On a couple of occasions, they caught a bus downtown and had a coffee in Starbucks, where there was a high risk he would run into kids from his school, but Emily had convinced him by then that even if it happened, no one would recognize him. Jack sometimes fantasized about running into Brad Philips and Brad chatting him up without realizing who he was. On a couple of occasions, Beacon Academy boys did come in while he was there with Emily.

Jack just hitched up his skirt and crossed his legs, looking the other way. Emily was proud of him. They always made sure they got home half an hour before their mother was due back from work, with plenty of time for Jack to clean off his make-up, brush out his hair, and change, either back into his school uniform or the jeans he habitually wore at home. Early on the morning of his 15th birthday, Emily slipped into his bedroom with a package tied with a bow. He was still in his pajamas.

“This is for Jackie,” she whispered conspiratorially, “happy birthday.”

Jackie was the name she had given him when he was in “girl mode." Jack untied the bow, tore open the wrapping, and gasped inside a red jersey dress with a tight bodice and very short flared skirt that they had both admired on the Topshop website a few days earlier. He had to swallow hard to stop himself from bursting into tears.

“Oh my God, Em,” he said, “thank you, thank you."

“Do you like it?” she asked unnecessarily.

“It’s wicked—totally wicked. I’m going to try it on right now.”

"Don't,” she said sharply.

"Mum might come in at any minute.” “I don’t care."

Emily was not ready to risk their secret being exposed, and she dissuaded him.

“You can put it on as soon as you get home from school, and I’ll come home early from the college so I can see you in it. I hope it’s the right size; I can’t change it if it’s not."

Jack missed the innuendo.

Emily was an experienced and successful shoplifter. When she found the dress on display in Topshop without a security tag, she whisked it into her bag within seconds. She wandered around the store for a few minutes to make sure she had not been spotted, then strolled out, giving the uniformed security guy at the door a big smile. Jack ran home from the school bus that afternoon, raced upstairs, stripped off in his bedroom, put on knickers and tights, and slipped his new dress over his head.

It fitted perfectly. He was still skipping joyfully around the house in it, frequently twirling to make the skirt flare out, when his sister got home.

When she saw he had paired it with red tights, she laughed and said it made him look like a lobster. He meekly accepted her suggestion that he should go upstairs and change into black tights. Jack was always ready to take advice from his sister, and a few days later, at her instigation, he was tottering around the house in high heels.

He was happy to wear Doc Martens with a dress (like most girls in Brighton), but Emily was determined to get him into what she called “fuck me” heels, which she considered the ultimate expression of femininity.

Her own heels She had a dozen pairs that were a size too small for him, but she chanced upon a perfect pair in Jack’s size in a charity shop with three-inch heels, platform soles, and a wide ankle strap in red leather, an almost perfect color match for his new dress. She popped them into her bag while the elderly lady tending the shop had her back turned, and she carried them home in triumph. Jack was thrilled. It took him several weeks before he could walk around in them without stumbling, but he persevered.

He realized that heels accentuated his long legs, particularly in a short skirt, and he could soon wear them as confidently as a catwalk model; he even claimed to Emily that they were actually comfortable, although she suspected he was lying. He was. They were agony, but he didn’t care.