He was so brave the first time he left the house with a face full of make up. The voice in his head had told him to be himself and after years of being lost in the fog he was finally able to realise that all he had ever wanted was to be a woman. The first time wasn’t really the first time. He’d been wearing makeup around the house for months. Today was the day though that he would face the world with a different kind of mask. Not the mask of a feigned masculinity that he wore with discomfort. This was a mask of feminine beauty. One that he would eventually use to trick guys into fucking him in darkened corners of abandoned alleyways and suburban drinking spots.
His family had been supportive. His mother welcomed this transition with open arms. His father’s arms were always open, but his mind was still yet to wrap itself around the concept that his boy was trying to be a girl. He worried that it was because he’d done something wrong as a father.
His sister was dying. This amplified his bravery. Only a real hero could face the world as he was with a traumatic event such as this in the offing. Her anorexia was wasting her away to a skeleton. They had all told her that she was beautiful and she wasn’t fat, but it fell on deaf ears and she stopped eating. It frustrated him to an extent. How could she be so deluded? She had the best family in the world supporting her and telling her that all the hateful things her mind had conjured up were untrue and that they loved her. He knew full well how supportive their parents were. They never stood in his way to transitioning. When the time came to hack off his cock, he knew they’d be there for him.
He stepped outside and the sun almost smashed the makeup off his face. He passed several men that gave him a look that he interpreted as desire. He felt that he had finally arrived. After years of repression and lying to himself, he was finally taking the first steps to being real. The heat was melting his makeup. He was glad he’d put it in his bag to reapply when he got to the shops. He knew this, of course. He knew that makeup needed to be reapplied. This made him braver. There were no baby steps with this and as soon as he could afford tits he would start wearing dresses. He’d been eyeing them off at the shops and this was where he was going.
He got a text from his mother. “Call me,” it said. He called his mother and she picked up after two rings. “Hi,” she said.
“What’s the matter?”
“Your sister is no good.”
“How bad is it?”
“The doctor said if she doesn’t put on weight soon she’ll die.”
“How fucking selfish.”
“Well, she’s causing no end of stress for you and Dad. All because of some delusion in her head that’s she’s fat. It’s retarded,” he said.
“She can’t help it,” said his mother.
“Anyway, Mum, I’m at the shops. I’ll call you later,” he said and then hung up. He was annoyed. His sister’s bullshit was distracting from his bravery. Maybe he’d wear the dress before he got the tits. That’d show them.
He got to the shops and the stares were obvious. He looked good. Straight guys would be easy to trick once he was fully decked out. He went into a clothing store. It felt good to go directly to the women’s section. There would be no more pretending. The shackles of biology were being cast aside and nothing would stop him from being what he wanted to be. A young shop assistant approached him. “Can I help you?” she asked. She was a young girl of about nineteen. She was wearing a floral dress and he thought she could do with losing a few pounds. Her makeup was also a tad too thick which was more an indication of her age than her skills with application. He imagined being her makeup mentor. “I’m looking for a dress. Something seductive. I’m planning on getting some fake tits and tricking straight guys into fucking me,” he said.
“Oh, well, this is mostly all we have,” she said and walked away. He knew the real him would be too much for some so he wasn’t offended at her departure. He took a few dresses from the rack and went and tried them on.
He picked three dresses. One was black with red flowers. Another was plain red and the other was plain black. He had made the decision while choosing that he would be getting D sized tits. He tried each dress on and stood back from the mirror that hung on the back wall of the changing cubicle. They all didn’t fit as well as he would have liked but he was able to imagine what he’d look like with fuller hips and tits. The top part of the dresses sagged down like the geriatric breasts of a ninety year old woman, but that did not deter him from his mission.
His phone buzzed. His mother had texted him again. “She’s in a coma,” it said. Then another one came through, “Can you come to the hospital?”
“Sure,” he replied. He left the change room and bought the dresses. The register girl stared at him the whole time. He interpreted this as jealousy. “I could fuck your dad,” he said to himself and giggled.
At the hospital his mother and father were waiting outside his sister’s room. A middle aged couple beaten down by circumstances that added more years to their physical features than what they had lived. Even in such a dark hour they could not help but be somewhat shocked at their son’s new appearance. In his rush to get to the hospital he had forgotten to reapply his makeup and now he looked more like a used up street whore who had been plying her trade in the rain than a young man transitioning to his truth. “What’s happened?” he asked his parents.
“The doctor said she’s dying,” said his mother.
“Well, that’s selfish,” he said.
“What?” said his father.
“I’m doing some pretty brave shit right now,” he said, raising his voice slightly.
“You’re walking around with makeup on your face and your sister is dying. That’s not brave. That’s stupid,” said his father.
“Look, she did this to herself. She was deluded. She wasn’t fat. We tried to help. She’s a narcissist. This is narcissism,” he said.
“You think you’re a woman. That’s deluded. We were willing to support you but the way you’re behaving right now is absurd,” said his mother.
“You’re not right in the head, son,” said his father.
“Fuck you all. I’ll show you! I’m getting tits and hacking off my cock! You’ll see!” he shouted and stomped off.
At home he wore the floral dress and reapplied his makeup. He started drinking early and by the time he thought he might like to go out and try to trick some straight guys into fucking him he was too drunk. He fell asleep on the couch with an empty bottle in his hands and mind full of plans that he was sick of waiting to implement.
He woke up in the heat of the morning sun that shone through the curtains he had forgotten to close the night before. He had dreamt of being gang banged by white trash in his new dress. His armpits stunk and his breath was even worse. He got up and turned on the computer. The tits and the cock hacking couldn’t wait. He’d show them. He started researching breast implants and that operation where they turn your cock into a vagina. It seemed involved. His phone buzzed. It was is mother. “She’s dead,” read the text.
“FUCK!! BITCH!!” he yelled. He then started dialling the number for the gender reassignment surgeon.